Galacto-Oligosaccharides: Production, Properties, Applications, and Significance as Prebiotics
Duarte P.M. Torres
Authors Torres and Rodrigues are with Biotempo—Biotechnology Consulting Ltd. Spinpark—Centro de Incubação de Base Tecnológica, Avepark, 4805-017 Guimarães, Portugal. Authors Torres, Teixeira, and Rodrigues are with IBB—Inst. for Biotechnology and Bioengineering, Centre of Biological Engineering, Univ. do Minho, 4710-057 Braga, Portugal. Author Torres is with Faculty of Nutrition and Food Sciences, Univ. of Porto, Rua Dr. Roberto Frias, 4200-465 Porto, Portugal. Author Gonçalves is with REQUIMTE, Dept. de Engenharia Química, Faculdade de Engenharia da Univ. do Porto, Rua Dr. Roberto Frias, 4200-465 Porto, Portugal. Direct inquiries to author Torres (E-mail: [email protected] ).
Search for more papers by this authorMaria do Pilar F. Gonçalves
Authors Torres and Rodrigues are with Biotempo—Biotechnology Consulting Ltd. Spinpark—Centro de Incubação de Base Tecnológica, Avepark, 4805-017 Guimarães, Portugal. Authors Torres, Teixeira, and Rodrigues are with IBB—Inst. for Biotechnology and Bioengineering, Centre of Biological Engineering, Univ. do Minho, 4710-057 Braga, Portugal. Author Torres is with Faculty of Nutrition and Food Sciences, Univ. of Porto, Rua Dr. Roberto Frias, 4200-465 Porto, Portugal. Author Gonçalves is with REQUIMTE, Dept. de Engenharia Química, Faculdade de Engenharia da Univ. do Porto, Rua Dr. Roberto Frias, 4200-465 Porto, Portugal. Direct inquiries to author Torres (E-mail: [email protected] ).
Search for more papers by this authorJosé A. Teixeira
Authors Torres and Rodrigues are with Biotempo—Biotechnology Consulting Ltd. Spinpark—Centro de Incubação de Base Tecnológica, Avepark, 4805-017 Guimarães, Portugal. Authors Torres, Teixeira, and Rodrigues are with IBB—Inst. for Biotechnology and Bioengineering, Centre of Biological Engineering, Univ. do Minho, 4710-057 Braga, Portugal. Author Torres is with Faculty of Nutrition and Food Sciences, Univ. of Porto, Rua Dr. Roberto Frias, 4200-465 Porto, Portugal. Author Gonçalves is with REQUIMTE, Dept. de Engenharia Química, Faculdade de Engenharia da Univ. do Porto, Rua Dr. Roberto Frias, 4200-465 Porto, Portugal. Direct inquiries to author Torres (E-mail: [email protected] ).
Search for more papers by this authorLígia R. Rodrigues
Authors Torres and Rodrigues are with Biotempo—Biotechnology Consulting Ltd. Spinpark—Centro de Incubação de Base Tecnológica, Avepark, 4805-017 Guimarães, Portugal. Authors Torres, Teixeira, and Rodrigues are with IBB—Inst. for Biotechnology and Bioengineering, Centre of Biological Engineering, Univ. do Minho, 4710-057 Braga, Portugal. Author Torres is with Faculty of Nutrition and Food Sciences, Univ. of Porto, Rua Dr. Roberto Frias, 4200-465 Porto, Portugal. Author Gonçalves is with REQUIMTE, Dept. de Engenharia Química, Faculdade de Engenharia da Univ. do Porto, Rua Dr. Roberto Frias, 4200-465 Porto, Portugal. Direct inquiries to author Torres (E-mail: [email protected] ).
Search for more papers by this authorDuarte P.M. Torres
Authors Torres and Rodrigues are with Biotempo—Biotechnology Consulting Ltd. Spinpark—Centro de Incubação de Base Tecnológica, Avepark, 4805-017 Guimarães, Portugal. Authors Torres, Teixeira, and Rodrigues are with IBB—Inst. for Biotechnology and Bioengineering, Centre of Biological Engineering, Univ. do Minho, 4710-057 Braga, Portugal. Author Torres is with Faculty of Nutrition and Food Sciences, Univ. of Porto, Rua Dr. Roberto Frias, 4200-465 Porto, Portugal. Author Gonçalves is with REQUIMTE, Dept. de Engenharia Química, Faculdade de Engenharia da Univ. do Porto, Rua Dr. Roberto Frias, 4200-465 Porto, Portugal. Direct inquiries to author Torres (E-mail: [email protected] ).
Search for more papers by this authorMaria do Pilar F. Gonçalves
Authors Torres and Rodrigues are with Biotempo—Biotechnology Consulting Ltd. Spinpark—Centro de Incubação de Base Tecnológica, Avepark, 4805-017 Guimarães, Portugal. Authors Torres, Teixeira, and Rodrigues are with IBB—Inst. for Biotechnology and Bioengineering, Centre of Biological Engineering, Univ. do Minho, 4710-057 Braga, Portugal. Author Torres is with Faculty of Nutrition and Food Sciences, Univ. of Porto, Rua Dr. Roberto Frias, 4200-465 Porto, Portugal. Author Gonçalves is with REQUIMTE, Dept. de Engenharia Química, Faculdade de Engenharia da Univ. do Porto, Rua Dr. Roberto Frias, 4200-465 Porto, Portugal. Direct inquiries to author Torres (E-mail: [email protected] ).
Search for more papers by this authorJosé A. Teixeira
Authors Torres and Rodrigues are with Biotempo—Biotechnology Consulting Ltd. Spinpark—Centro de Incubação de Base Tecnológica, Avepark, 4805-017 Guimarães, Portugal. Authors Torres, Teixeira, and Rodrigues are with IBB—Inst. for Biotechnology and Bioengineering, Centre of Biological Engineering, Univ. do Minho, 4710-057 Braga, Portugal. Author Torres is with Faculty of Nutrition and Food Sciences, Univ. of Porto, Rua Dr. Roberto Frias, 4200-465 Porto, Portugal. Author Gonçalves is with REQUIMTE, Dept. de Engenharia Química, Faculdade de Engenharia da Univ. do Porto, Rua Dr. Roberto Frias, 4200-465 Porto, Portugal. Direct inquiries to author Torres (E-mail: [email protected] ).
Search for more papers by this authorLígia R. Rodrigues
Authors Torres and Rodrigues are with Biotempo—Biotechnology Consulting Ltd. Spinpark—Centro de Incubação de Base Tecnológica, Avepark, 4805-017 Guimarães, Portugal. Authors Torres, Teixeira, and Rodrigues are with IBB—Inst. for Biotechnology and Bioengineering, Centre of Biological Engineering, Univ. do Minho, 4710-057 Braga, Portugal. Author Torres is with Faculty of Nutrition and Food Sciences, Univ. of Porto, Rua Dr. Roberto Frias, 4200-465 Porto, Portugal. Author Gonçalves is with REQUIMTE, Dept. de Engenharia Química, Faculdade de Engenharia da Univ. do Porto, Rua Dr. Roberto Frias, 4200-465 Porto, Portugal. Direct inquiries to author Torres (E-mail: [email protected] ).
Search for more papers by this authorAbstract
Abstract: Galacto-oligosaccharides (GOS) have now been definitely established as prebiotic ingredients after in vitro and animal and human in vivo studies. Currently, GOS are produced by glycoside hydrolases (GH) using lactose as substrate. Converting lactose into GOS by GH results in mixtures containing GOS of different degrees of polymerization (DP), unreacted lactose, and monomeric sugars (glucose and galactose). Recent and future developments in the production of GOS aim at delivering purer and more efficient mixtures. To produce high-GOS-content mixtures, GH should not only have good ability to catalyze the transgalactosylation reaction relative to hydrolysis, but also have low affinity for the GOS formed relative to the affinity for lactose. In this article, several microbial GH, proposed for the synthesis of GOS, are hierarchized according to the referred performance indicators. In addition, strategies for process improvement are discussed. Besides the differences in purity of GOS mixtures, differences in the position of the glycosidic linkages occur, because different enzymes have different regiochemical selectivity. Depending on oligosaccharide composition, GOS products will vary in terms of prebiotic activity, as well as other physiological effects. This review focuses on GOS production from synthesis to purification processes. Physicochemical characteristics, physiological effects, and applications of these prebiotic ingredients are summarized. Regulatory aspects of GOS-containing food products are also highlighted with emphasis on the current process of health claims evaluation in Europe.
References
- Adam AC, Rubio-Texeira M, Polaina J. 2004. Lactose: the milk sugar from a biotechnological perspective. Crit Rev Food Sci Nutr 44(7–8): 553–7.
- Affertsholt-Allen T. 2007. Market developments and industry challenges for lactose and lactose derivatives. IDF Symposium “Lactose and its Derivatives.” Moscow . Available from: http://lactose.ru/present/1Tage_Affertsholt-Allen.pdf . Accessed Sept 30, 2009.
- Akiyama K, Takase M, Horikoshi K, Okonogi S. 2001. Production of galactooligosaccharides from lactose using a beta-glucosidase from Thermus sp Z-1. Biosci Biotechnol Biochem 65(2): 438–41.
- Albayrak N, Yang ST. 2002a. Immobilization of Aspergillus oryzae beta-galactosidase on tosylated cotton cloth. Enzyme Microb Technol 31(4): 371–83.
- Albayrak N, Yang ST. 2002b. Immobilization of beta-galactosidase on fibrous matrix by polyethyleneimine for production of galacto-oligosaccharides from lactose. Biotechnol Prog 18(2): 240–51.
- Albayrak N, Yang ST. 2002c. Production of galacto-oligosaccharides from lactose by Aspergillus oryzae beta-galactosidase immobilized on cotton cloth. Biotechnol Bioengr 77(1): 8–19.
- Alles MS, Hartemink R, Meyboom S, Harryvan JL, Van Laere KMJ, Nagengast FM, Hautvast JGAJ. 1999. Effect of transgalactooligosaccharides on the composition of the human intestinal microflora and on putative risk markers for colon cancer. Am J Clin Nutr 69(5): 980–91.
- [AOAC] Assn. of Official Analytical Chemists. 1995. Method 985.29—Total dietary fiber in foods, enzymatic-gravimetric method. In: P Cunniff, editor. Official methods of analysis of AOAC Intl. 16th ed. Arlington , Va. : AOAC.
- [AOAC]Assn. of Official Analytical Chemists. 2005. Method 2001.02—determination of trans-galactooligosaccharides (TGOS) in selected food products. In: GW Latimer, W Horwitz, editors. Official methods of analysis of AOAC Intl. 18th ed. Gaithersburg , Md. : AOAC.
- Aronson M. 1952. Transgalactosidation during lactose hydrolysis. Arch Biochem Biophys 39(2): 370–8.
- Aslan Y, Tanriseven A. 2007. Immobilization of Pectinex Ultra SP-L to produce galactooligosaccharides. J Mol Catal B Enzym 45(3–4): 73–7.
- Asp NG, Burvall A, Dahlqvist A, Hallgren P, Lundblad A. 1980. Oligosaccharide formation during hydrolysis of lactose with Saccharomyces lactis lactase (Maxilact). 2. Oligosaccharide structures. Food Chem 5(2): 147–53.
- Backhed F, Ley RE, Sonnenburg JL, Peterson DA, Gordon JI. 2005. Host-bacterial mutualism in the human intestine. Science 307(5717): 1915–20.
- Bakker-Zierikzee AM, Alles MS, Knol J, Kok FJ, Tolboom JJM, Bindels JG. 2005. Effects of infant formula containing a mixture of galacto- and fructo-oligosaccharides or viable Bifidobacterium animalis on the intestinal microflora during the first 4 months of life. Br J Nutr 94(5): 783–90.
- Ballio A, Russi S. 1960. Chromatographic fractionation and chemical characterization of some oligosaccharides synthesized from lactose by Penicillium chrysogenum thom. J Chromatogr A 4: 117–29.
- Biggs P, Parsons CM, Fahey GC. 2007. The effects of several oligosaccharides on growth performance, nutrient digestibilities, and cecal microbial populations in young chicks. Poult Sci 86: 2327–36.
- Bockmühl D, Jassoy C, Nieveler S, Scholtyssek R, Wadle A, Waldmann-Laue M. 2007. Prebiotic cosmetics: an alternative to antibacterial products. Int J Cosmet Sci 29(1): 63–4.
- Boehm G, Moro G. 2008. Structural and functional aspects of prebiotics used in infant nutrition. J Nutr 138(9): 1818S–28.
- Boehm G, Stahl B, Jelinek J, Knol J, Miniello V, Moro GE. 2005. Prebiotic carbohydrates in human milk and formulas. Acta Paediatr 94: 18–21.
- Boon MA, Van Der Oost J, De Vos WM, Janssen AEM, Van't Riet K. 1998. Synthesis of oligosaccharides catalyzed by thermostable beta-glucosidase from Pyrococcus furiosus. Appl Biochem Biotechnol 75(2–3): 269–78.
- Boon MA, Janssen AEM, Van Der Padt A. 1999. Modelling and parameter estimation of the enzymatic synthesis of oligosaccharides by beta-galactosidase from Bacillus circulans. Biotechnol Bioengr 64(5): 558–67.
- Boon MA, Janssen AEM, Van't Riet K. 2000a. Effect of temperature and enzyme origin on the enzymatic synthesis of oligosaccharides. Enzyme Microb Technol 26(2–4): 271–81.
- Boon MA, Van't Riet K, Janssen AEM. 2000b. Enzymatic synthesis of oligosaccharides: product removal during a kinetically controlled reaction. Biotechnol Bioengr 70(4): 411–20.
- Bouhnik Y, Flourie B, D’Agay-Abensour L, Pochart P, Gramet G, Durand M, Rambaud J-C. 1997. Administration of transgalacto-oligosaccharides increases fecal bifidobacteria and modifies colonic fermentation metabolism in healthy humans. J Nutr 127(3): 444–8.
- Bruins ME, Strubel M, Van Lieshout JFT, Janssen AEM, Boom RM. 2003. Oligosaccharide synthesis by the hyperthermostable beta-glucosidase from Pyrococcus furiosus: kinetics and modelling. Enzyme Microb Technol 33(1): 3–11.
- Burr G, Hume M, Neill WH, Gatlin DM. 2008. Effects of prebiotics on nutrient digestibility of a soybean-meal-based diet by red drum Sciaenops ocellatus (Linnaeus). Aquac Res 39(15): 1680–6.
- Burvall A, Asp NG, Dahlqvist A. 1979. Oligosaccharide formation during hydrolysis of lactose with Saccharomyces lactis lactase (Maxilact). 1. Quantitative aspects. Food Chem 4(4): 243–50.
- Cantarel BL, Coutinho PM, Rancurel C, Bernard T, Lombard V, Henrissat B. 2009. The Carbohydrate-Active EnZymes database (CAZy): an expert resource for Glycogenomics. Nucleic Acids Res 37: D233–38.
- Cardelle-Cobas A, Villamiel M, Olano A, Corzo N. 2008. Study of galacto-oligosaccharide formation from lactose using pectinex ultra SP-L. J Sci Food Agric 88(6): 954–61.
- CAZy—Carbohydrate-Active Enzymes [internet]. Marseille , France : Glycogenomics group—Architecture Et Fonction Des Macromolécules Biologiques c1998-2010. Available from: http://www.cazy.org/Glycoside-Hydrolases.html . Accessed Sept 30, 2009.
- Chen CW, Ou-Yang CC, Yeh CW. 2003. Synthesis of galactooligosaccharides and transgalactosylation modeling in reverse micelles. Enzyme Microb Technol 33(4): 497–507.
- Chen SX, Wei DZ, Hu ZH. 2001. Synthesis of galacto-oligosaccharides in AOT/isooctane reverse micelles by beta-galactosidase. J Mol Catal B Enzym 16(2): 109–14.
- Cheng CC, Yu MC, Cheng TC, Sheu DC, Duan KJ, Tai WL. 2006a. Production of high-content galacto-oligosaccharide by enzyme catalysis and fermentation with Kluyveromyces marxianus. Biotechnol Lett 28(11): 793–7.
- Cheng CC, Yu MC, Cheng TC, Sheu DC, Duan KJ, Tai WL. 2006b. Production of high-content galacto-oligosaccharide by enzyme catalysis and fermentation with Kluyveromyces marxianus. Biotechnol Lett 28(22): 1863–64.
- Cheng TC, Duan KJ, Sheu DC. 2006c. Application of tris(hydroxymethyl)phosphine as a coupling agent for beta-galactosidase immobilized on chitosan to produce galactooligosaccharides. J Chem Technol Biotechnol 81(2): 233–6.
- Cho YJ, Shin HJ, Bucke C. 2003. Purification and biochemical properties of a galactooligosaccharide producing beta-galactosidase from Bullera singularis. Biotechnol Lett 25(24): 2107–11.
- Chockchaisawasdee S, Athanasopoulos VI, Niranjan K, Rastall RA. 2005. Synthesis of galacto-oligosaccharide from lactose using beta-galactosidase from Kluyveromyces lactis: studies on batch and continuous UF membrane-fitted bioreactors. Biotechnol Bioengr 89(4): 434–43.
- Choi JJ, Oh EJ, Lee YJ, Suh DS, Lee JH, Lee SW, Shin HT, Kwon ST. 2003. Enhanced expression of the gene for beta-glycosidase of Thermus caldophilus GK24 and synthesis of galacto-oligosaccharides by the enzyme. Biotechnol Appl Biochem 38: 131–6.
- Chonan O, Shibahara-Sone H, Takahashi R, Ikeda M, Kikuchi-Hayakawa H, Ishikawa F, Kimura K, Matsumoto K. 2004. Undigestibility of galactooligosaccharides. J Jpn Soc Food Sci 51(1): 28–33.
- Coulier L, Timmermans J, Bas R, Van Den Dool R, Haaksman I, Klarenbeck B, Slaghek T, Van Dongen W. 2009. In-depth characterization of prebiotic galacto-oligosaccharides by a combination of analytical techniques. J Agric Food Chem 57(18): 8488–95.
- Coutinho PM, Deleury E, Davies GJ, Henrissat B. 2003. An evolving hierarchical family classification for glycosyltransferases. J Mol Biol 328(2): 307–17.
10.1016/S0022-2836(03)00307-3 Google Scholar
- Crittenden RG, Playne MJ. 2002. Purification of food-grade oligosaccharides using immobilised cells of Zymomonas mobilis. Appl Microbiol Biotechnol 58(3): 297–302.
- Crout DHG, Vic G. 1998. Glycosidases and glycosyl transferases in glycoside and oligosaccharide synthesis. Curr Opin Chem Biol 2(1): 98–111.
- Cruz R, Cruz VD, Belote JG, Khenayfes MD, Dorta C, Oliveira LHD, Ardiles E, Galli A. 1999. Production of transgalactosylated oligosaccharides (TOS) by galactosyltransferase activity from Penicillium simplicissimum. Bioresour Technol 70(2): 165–71.
- Cummings JH. 1995. Short chain fatty acids. In: GR Gibson, GT MacFarlane, editors. Human colonic bacteria: role in nutrition, physiology and health. Boca Raton , Fla. : CRC Press. p 101–30.
- Cummings JH, Roberfroid MB, Andersson H, Barth C, FerroLuzzi A, Ghoos Y, Gibney M, Hermonsen K, James WPT, Korver O, Lairon D, Pascal G, Voragen AGS. 1997. A new look at dietary carbohydrate: chemistry, physiology and health. Eur J Clin Nutr 51(7): 417–23.
- Czermak P, Ebrahimi M, Grau K, Netz S, Sawatzki G, Pfromm PH. 2004. Membrane-assisted enzymatic production of galactosyl-oligosaccharides from lactose in a continuous process. J Memb Sci 232(1–2): 85–91.
- Davies G, Henrissat B. 1995. Structures and mechanisms of glycosyl hydrolases. Structure 3(9): 853–9.
- Del-Val MI, Otero C. 2003. Biphasic aqueous media containing polyethylene glycol for the enzymatic synthesis of oligosaccharides from lactose. Enzyme Microb Technol 33(1): 118–26.
- Del-Val MI, Hill CG, Jimenez-Barbero J, Otero C. 2001. Selective enzymatic synthesis of 6 ‘-galactosyl lactose by Pectinex Ultra SP in water. Biotechnol Lett 23(23): 1921–4.
- Depeint F, Tzortzis G, Vulevic J, I’Anson K, Gibson GR. 2008. Prebiotic evaluation of a novel galactooligosaccharide mixture produced by the enzymatic activity of Bifidobacterium bifidum NCIMB 41171, in healthy humans: a randomized, double-blind, crossover, placebo-controlled intervention study. Am J Clin Nutr 87(3): 785–91.
- De Roode BM, Franssen ACR, Van Der Padt A, Boom RM. 2003. Perspectives for the industrial enzymatic production of glycosides. Biotechnol Prog 19(5): 1391–402.
- De Slegte J. 2002. Determination of trans-galactooligosaccharides in selected food products by ion-exchange chromatography: collaborative study. J AOAC Int 85(2): 417–23.
- DeVries JW. 2004. Dietary fiber: the influence of definition on analysis and regulation. J AOAC Int 87(3): 682–706.
- Dombou M, Tomioka I, Tsurutani R, Kitabatake S, Nakajima H, inventors; Unitika Ltd., assignee. 1992 Nov 11. Method for production of a growth factor for Bifidobacterium sp. European patent 0 262 858 B1.
- Drueckhammer DG, Hennen WJ, Pederson RL, Barbas CF, Gautheron CM, Krach T, Wong CH. 1991. Enzyme catalysis in synthetic carbohydrate-chemistry. Synthesis-Stuttgart (7): 499–525.
- Dumortier V, Brassart C, Bouquelet S. 1994. Purification and properties of a beta-d-galactosidase from Bifidobacterium bifidum exhibiting a transgalactosylation reaction. Biotechnol Appl Biochem 19: 341–54.
- Ebrahimi M, Engel L, Peter S, Grau K, Czermak P. 2006a. Membrane-supported enzymatic synthesis of galactosyl-oligosaccharides. Desalination 200(1–3): 509–10.
- Ebrahimi M, Gonzalez R, Czermak P. 2006b. Experimental and theoretical study of galactosyl-oligosaccharides formation in CRMR by thermostable mesophilic enzymes. Desalination 200(1–3): 686–8.
- EFSA: Consolidated list of Article 13 health claims List of references received by EFSA—Part 1 [internet]. Parma : Scientific Panel on Dietetic Products, Nutrition and Allergies Unit; c25 February 2010a. Available from: http://www.efsa.europa.eu/en/ndaclaims13/docs/art13ref1.pdf . Accessed Mar 25, 2010.
- EFSA: Consolidated list of Article 13 health claims List of references received by EFSA—Part 3 [internet]. Parma : Scientific Panel on Dietetic Products, Nutrition and Allergies Unit; c25 February 2010b. Available from: http://www.efsa.europa.eu/en/ndaclaims13/docs/art13ref3.pdf . Accessed Mar 25, 2010.
- Engel L, Ebrahimi M, Czermak P. 2008. Membrane chromatography reactor system for the continuous synthesis of galactosyl-oligosaccharides. Desalination 224(1–3): 46–51.
- European Directive. 2008. Commission Directive 2008/100/EC of 28 October 2008 amending Council Directive 90/496/EEC on nutrition labelling for foodstuffs as regards recommended daily allowances, energy conversion factors and definitions. Official J Eur Union L 285: 9–12.
- European Regulation. 2006. Regulation (EC) 1924/2006 of the European Parliament and of the Council of 20 December 2006 on nutrition and health claims made on foods. Official J Eur Union L 12: 3–18.
- Fanaro S, Chierici R, Guerrini P, Vigi V. 2003. Intestinal microflora in early infancy: composition and development. Acta Paediatr 92: 48–55.
- Fanaro S, Boehm G, Garssen J, Knol J, Mosca F, Stahl B, Vigi V. 2005. Galacto-oligosaccharides and long-chain fructo-oligosaccharides as prebiotics in infant formulas: a review. Acta Paediatr 94: 22–6.
- Fanaro S, Marten B, Bagna R, Vigi V, Fabris C, Pena-Quintana L, Arguelles F, Scholz-Ahrens KE, Sawatzki G, Zelenka R, Schrezenmeir J, De Vrese M, Bertino E. 2009. Galacto-oligosaccharides are bifidogenic and safe at weaning: a double-blind randomized multicenter study. J Pediatr Gastr Nutr 48(1): 82–8.
- Feng YM, Chang XL, Wang WH, Ma RY. 2009. Separation of galacto-oligosaccharides mixture by nanofiltration. J Taiwan Inst Chem E 40(3): 326–32.
- Foda MI, Lopez-Leiva M. 2000. Continuous production of oligosaccharides from whey using a membrane reactor. Process Biochem 35(6): 581–7.
- Fox PF. 2009. Lactose: Chemistry and Properties. In: PLH McSweeney, PF Fox, editors. Lactose, water, salts and minor constituents. 3rd ed. New York : Springer. p 1–15.
- Ganzle MG, Haase G, Jelen P. 2008. Lactose: crystallization, hydrolysis and value-added derivatives. Int Dairy J 18(7): 685–94.
- Gaur R, Pant H, Jain R, Khare SK. 2006. Galacto-oligosaccharide synthesis by immobilized Aspergillus oryzae beta-galactosidase. Food Chem 97(3): 426–30.
- Gekas V, Lopez-Leiva M. 1985. Hydrolysis of lactose—a literature-review. Process Biochem 20(1): 2–12.
- Gibson GR, Roberfroid MB. 1995. Dietary modulation of the human colonic microbiota—introducing the concept of prebiotics. J Nutr 125(6): 1401–12.
- Gibson GR, Probert HM, Van Loo J, Rastall RA, Roberfroid MB. 2004a. Dietary modulation of the human colonic microbiota: updating the concept of prebiotics. Nutr Res Rev 17(2): 259–75.
- Gibson GR, Rabiu B, Rycroft CE, Rastall RA. 2004b. trans-Galactooligosaccharides as prebiotics. In: C Shortt, J O’Brien, editors. Handbook of functional dairy products. Boca Raton , Fla. : CRC Press. p 91–108.
- Gill SR, Pop M, DeBoy RT, Eckburg PB, Turnbaugh PJ, Samuel BS, Gordon JI, Relman DA, Fraser-Liggett CM, Nelson KE. 2006. Metagenomic analysis of the human distal gut microbiome. Science 312(5778): 1355–9.
- Gorin PAJ, Phaff HJ, Spencer JFT. 1964. Structures of galactosyl-lactose + galactobiosyl-lactose produced from lactose by Sporobolomyces singularis. Can J Chem 42(6): 1341–4.
- Gorin PAJ, Haskins RH, Westlake DW. 1966. A new galactobiosyl glucose formed from lactose by Chaetomium globosum. Can J Chem 44(17): 2083–6.
- Goulas A, Tzortzis G, Gibson GR. 2007a. Development of a process for the production and purification of alpha- and beta-galactooligosaccharides from Bifobacterium bifidum NCIMB 41171. Int Dairy J 17(6): 648–56.
- Goulas AK, Kapasakalidis PG, Sinclair HR, Rastall RA, Grandison AS. 2002. Purification of oligosaccharides by nanofiltration. J Membrane Sci 209(1): 321–35.
- Goulas AK, Grandison AS, Rastall RA. 2003. Fractionation of oligosaccharides by nanofiltration. J Sci Food Agric 83(7): 675–80.
- Goulas TK, Goulas AK, Tzortzis G, Gibson GR. 2007b. Molecular cloning and comparative analysis of four beta-galactosidase genes from Bifidobacterium bifidum NCIMB41171. Appl Microbiol Biotechnol 76: 1365–72.
- Greenberg NA, Mahoney RR. 1983. Formation of oligosaccharides by beta-galactosidase from Streptococcus thermophilus. Food Chem 10(3): 195–204.
- Grisdale-Helland B, Helland SJ, Gatlin DM. 2008. The effects of dietary supplementation with mannanoligosaccharide, fructooligosaccharide or galactooligosaccharide on the growth and feed utilization of Atlantic salmon (Salmo salar). Aquaculture 283(1–4): 163–67.
- GTC Nutrition. 2009. Galactooligosaccharide GRAS notice [internet]. Available from: http://www.accessdata.fda.gov/scripts/fcn/gras_notices/grn000285.pdf . Accessed Sept 30, 2009.
- Hansson T, Adlercreutz P. 2001. Optimization of galactooligosaccharide production from lactose using beta-glycosidases from hyperthermophiles. Food Biotechnol 15(2): 79–97.
- Hansson T, Kaper T, Van Der Oost J, De Vos WM, Adlercreutz P. 2001. Improved oligosaccharide synthesis by protein engineering of beta-glucosidase CelB from hyperthermophilic Pyrococcus furiosus. Biotechnol Bioengr 73(3): 203–10.
- Harmsen HJM, Wildeboer-Veloo ACM, Raangs GC, Wagendorp AA, Klijn N, Bindels JG, Welling GW. 2000. Analysis of intestinal flora development in breast-fed and formula-fed infants by using molecular identification and detection methods. J Pediatr Gastr Nutr 30(1): 61–7.
- Hartemink R, VanLaere KMJ, Peeters C, Nout MJR, Rombouts FM. 1997. In vitro cariogenicity of trans-galactosyl-oligosaccharides. Lett Appl Microbiol 25(1): 38–42.
- Henrissat B. 1991. A classification of glycosyl hydrolases based on amino-acid-sequence similarities. Biochem J 280: 309–16.
- Henrissat B, Bairoch A. 1996. Updating the sequence-based classification of glycosyl hydrolases. Biochem J 316: 695–6.
- Hernandez O, Ruiz-Matute AI, Olano A, Moreno FJ, Sanz ML. 2009. Comparison of fractionation techniques to obtain prebiotic galactooligosaccharides. Int Dairy J 19(9): 531–6.
- Houdijk J, Bosch M, Verstegen M, Tamminga S. 1997. Type and level of dietary oligosaccharides change volatile fatty acid composition in ileal chyme of young pigs. In: JP Laplace, C Février, A Barbeau, editors. Digestive physiology in Pigs. EAAP Publications. p 475–8.
- Houdijk JGM, Bosch MW, Verstegen MWA, Berenpas HJ. 1998. Effects of dietary oligosaccharides on the growth performance and faecal characteristics of young growing pigs. Anim Feed Sci Technol 71(1–2): 35–48.
- Hsu CA, Lee SL, Chou CC. 2007. Enzymatic production of galactooligosaccharides by beta-galactosidase from Bifidobacterium longum BCRC 15708. J Agric Food Chem 55(6): 2225–30.
- Huber RE, Kurz G, Wallenfels K. 1976. Quantitation of factors which affect hydrolase and transgalactosylase activities of beta-galactosidase (Escherichia coli) on lactose. Biochemistry 15(9): 1994–2001.
- Huh KT, Toba T, Adachi S. 1990. Oligosaccharide formation during the hydrolysis of lactose with hydrochloric-acid and cation-exchange resin. Food Chem 38(4): 305–14.
- Huh KT, Toba T, Adachi S. 1991. Oligosaccharide structures formed during acid-hydrolysis of lactose. Food Chem 39(1): 39–49.
- Hung MN, Lee BH. 2002. Purification and characterization of a recombinant beta-galactosidase with transgalactosylation activity from Bifidobacterium infantis HL96. Appl Microbiol Biotechnol 58(4): 439–45.
- Hung MN, Xia ZC, Hu NT, Lee BH. 2001. Molecular and biochemical analysis of two beta-galactosidases from Bifidobacterium infantis HL96. Appl Environ Microbiol 67(9): 4256–63.
- Iqbal MF, Cheng YF, Zhu WY, Zeshan B. 2008. Mitigation of ruminant methane production: current strategies, constraints and future options. World J Microbiol Biotechnol 24(12): 2747–55.
- Ishikawa E, Sakai T, Ikemura H, Matsumoto K, Abe H. 2005. Identification, cloning, and characterization of a Sporobolomyces singularis beta-galactosidase-like enzyme involved in galacto-oligosaccharide production. J Biosci Bioengr 99(4): 331–9.
- Ito M, Deguchi Y, Miyamori A, Matsumoto K, Kikuchi H, Kobayashi Y, Yajima T, Kan T. 1990. Effects of administration of galactooligosaccharides on the human faecal microflora, stool weight and abdominal sensation. Microb Ecol Health Dis 3(6): 285–92.
10.3109/08910609009140251 Google Scholar
- Ito M, Deguchi Y, Matsumoto K, Kimura M, Onodera N, Yajima T. 1993. Influence of galactooligosaccharides on the human fecal microflora. J Nutr Sci Vitaminol 39(6): 635–40.
- Iwasaki K, Nakajima M, Nakao S. 1996. Galacto-oligosaccharide production from lactose by an enzymic batch reaction using beta-galactosidase. Process Biochem 31(1): 69–76.
- Jeon IJ, Mantha VR. 1985. High-performance liquid-chromatography analysis of oligosaccharides formed during beta-galactosidase action on lactose. J Dairy Sci 68(3): 581–8.
- Ji ES, Park NH, Oh DK. 2005. Galacto-oligosaccharide production by a thermostable recombinant beta-galactosidase from Thermotoga maritima. World J Microbiol Biotechnol 21(5): 759–64.
- Jorgensen F, Hansen OC, Stougaard P. 2001. High-efficiency synthesis of oligosaccharides with a truncated beta-galactosidase from Bifidobacterium bifidum. Appl Microbiol Biotechnol 57(5–6): 647–52.
- Jung SJ, Lee BH. 2008. Production and application of galacto-oligosaccharides from lactose by a recombinant beta-galactosidase of Bifidobacterium infantis overproduced by Pichia pastoris. Food Sci Technol 17(3): 514–8.
- Jung SJ, Houde R, Baurhoo B, Zhao X, Lee BH. 2008. Effects of galacto-oligosaccharides and a bifidobacteria lactis-based probiotic strain on the growth performance and fecal microflora of broiler chickens. Poult Sci 87(9): 1694–9.
- Katta Y, Ohkuma K, Satouchi M, Takahashi R, Yamamoto T, inventors; Matsutani Chemical Industries Co., Ltd., assignee. 2000. Method for preparing galacto-oligosaccharides. European patent 0 435 657 B1.
- Kim CS, Ji ES, Oh DK. 2004. Characterization of a thermostable recombinant beta-galactosidase from Thermotoga maritima. J Appl Microbiol 97(5): 1006–14.
- Kim JH, Lee DH, Lee JS. 2001. Production of galactooligosaccharide by beta-galactosidase from Kluyveromyces marxianus var lactis OE-20. Biotechnol Bioprocess Engr 6(5): 337–40.
- Knol J, Boehm G, Lidestri M, Negretti F, Jelinek J, Agosti M, Stahl B, Marini A, Mosca F. 2005a. Increase of faecal bifidobacteria due to dietary oligosaccharides induces a reduction of clinically relevant pathogen germs in the faeces of formula-fed preterm infants. Acta Paediatr 94: 31–3.
- Knol J, Scholtens P, Kafka C, Steenbakkers J, Gross S, Helm K, Klarczyk M, Schopfer H, Bockler HM, Wells J. 2005b. Colon microflora in infants fed formula with galacto- and fructo-oligosaccharides: more like breast-fed infants. J Pediatr Gastr Nutr 40(1): 36–42.
- Koshland DE. 1953. Stereochemistry and the mechanism of enzymatic reactions. Biol Rev Camb Philos Soc 28(4): 416–36.
- Krutmann J. 2009. Pre- and probiotics for human skin. J Dermatol Sci 54(1): 1–5.
- Kunz C, Rudloff S, Baier W, Klein N, Strobel S. 2000. Oligosaccharides in human milk: Structural, functional, and metabolic aspects. Annu Rev Nutr 20: 699–722.
- Lairson LL, Henrissat B, Davies GJ, Withers SG. 2008. Glycosyltransferases: Structures, functions, and mechanisms. Annu Rev Biochem 77: 521–55.
- Leiva MHL, Guzman M. 1995. Formation of oligosaccharides during enzymatic-hydrolysis of milk whey permeates. Process Biochem 30(8): 757–62.
- Li Y, Lu L, Wang H, Xu X, Xiao M. 2009. Cell surface engineering of a beta-galactosidase for galactooligosaccharide synthesis. Appl Environ Microbiol 75(18): 5938–42.
- Li ZY, Xiao M, Lu LL, Li YM. 2008. Production of non-monosaccharide and high-purity galactooligosaccharides by immobilized enzyme catalysis and fermentation with immobilized yeast cells. Process Biochem 43(8): 896–9.
- Lifran EV, Hourigan JA, Sleigh RW. 2009. Lactose derivatives: turning waste into functional foods. Aust J Dairy Technol 64(1): 89–93.
- Lu LL, Xiao M, Xu XD, Li ZY, Li YM. 2007. A novel beta-galactosidase capable of glycosyl transfer from Enterobacter agglomerans B1. Biochem Biophys Res Commun 356(1): 78–84.
- Lu LL, Xiao M, Li ZY, Li YM, Wang FS. 2009. A novel transglycosylating beta-galactosidase from Enterobacter cloacae B5. Process Biochem 44(2): 232–6.
- Lupp C, Finlay BB. 2005. Intestinal microbiota. Curr Biol 15(7): R235–36.
- Ly HD, Withers SG. 1999. Mutagenesis of glycosidases. Annu Rev Biochem 68: 487–522.
- Macfarlane GT, Steed H, Macfarlane S. 2008. Bacterial metabolism and health-related effects of galacto-oligosaccharides and other prebiotics. J Appl Microbiol 104(2): 305–44.
- Macfarlane S, Macfarlane GT, Cummings JH. 2006. Review article: prebiotics in the gastrointestinal tract. Aliment Pharmacol Ther 24(5): 701–14.
- Maischberger T, Nguyen TH, Sukyai P, Kittl R, Riva S, Ludwig R, Haltrich D. 2008. Production of lactose-free galacto-oligosaccharide mixtures: comparison of two cellobiose dehydrogenases for the selective oxidation of lactose to lactobionic acid. Carbohydr Res 343(12): 2140–7.
- Martinez-Villaluenga C, Cardelle-Cobas A, Corzo N, Lano A, Villamiel M. 2008. Optimization of conditions for galactooligosaccharide synthesis during lactose hydrolysis by beta-galactosidase from Kluyveromyces lactis (Lactozym 3000 L HP G). Food Chem 107(1): 258–64.
- Matella NJ, Dolan KD, Lee YS. 2006. Comparison of galactooligosaccharide production in free-enzyme ultrafiltration and in immobilized-enzyme systems. J Food Sci 71(7): C363–8.
- Maugard T, Gaunt D, Legoy MD, Besson T. 2003. Microwave-assisted synthesis of galacto-oligosaccharides from lactose with immobilized beta-galactosidase from Kluyveromyces lactis. Biotechnol Lett 25(8): 623–9.
- McCartney AL, Gibson GR. 2006. The normal microbiota of the human gastrointestinal tract: history of analysis, succession, and dietary influences. In: AC Ouwehand, EE Vaughan, editors. Gastrointestinal microbiology. New York : Taylor & Francis Group. p 51–73.
10.3109/9781420014952-4 Google Scholar
- Modesto M, D’Aimmo MR, Stefanini I, Trevisi P, De Filippi S, Casini L, Mazzoni M, Bosi P, Biavati B. 2009. A novel strategy to select Bifidobacterium strains and prebiotics as natural growth promoters in newly weaned pigs. Livest Sci 122(2–3): 248–58.
- Moller PL, Jorgensen F, Hansen OC, Madsen SM, Stougaard P. 2001. Intra- and extracellular beta-galactosidases from Bifidobacterium bifidum and B. infantis: molecular cloning, heterologous expression, and comparative characterization. Appl Environ Microbiol 67(5): 2276–83.
- Monsan P, Paul F. 1995. Enzymatic-synthesis of oligosaccharides. FEMS Microbiol Rev 16(2–3): 187–92.
- Montanes F, Olano A, Reglero G, Ibanez E, Fornari T. 2009. Supercritical technology as an alternative to fractionate prebiotic galactooligosaccharides. Sep Purif Technol 66(2): 383–9.
- Moro GE, Stahl B, Fanaro S, Jelinek J, Boehm G, Coppa GV. 2005. Dietary prebiotic oligosaccharides are detectable in the faeces of formula-fed infants. Acta Paediatr 94: 27–30.
- Mozaffar Z, Nakanishi K, Matsuno R, Kamikubo T. 1984. Purification and properties of beta-galactosidases from Bacillus circulans. Agric Biol Chem 48(12): 3053–61.
- Mozaffar Z, Nakanishi K, Matsuno R. 1986. Continuous production of galacto-oligosaccharides from lactose using immobilized beta-galactosidase from Bacillus circulans. Appl Microbiol Biotechnol 25(3): 224–8.
- Mozaffar Z, Nakanishi K, Matsuno R. 1987. Effect of glutaraldehyde on oligosaccharide production by beta-galactosidase from Bacillus circulans. Appl Microbiol Biotechnol 25(5): 426–29.
- Mwenya B, Santoso B, Sar C, Gamo Y, Kobayashi T, Arai I, Takahashi J. 2004a. Effects of including beta 1-4 galacto-oligosaccharides, lactic acid bacteria or yeast culture on methanogenesis as well as energy and nitrogen metabolism in sheep. Anim Feed Sci Technol 115(3–4): 313–26.
- Mwenya B, Zhou X, Santoso B, Sar C, Gamo Y, Kobayashi T, Takahashi J. 2004b. Effects of probiotic-vitacogen and beta 1-4 galacto-oligosaccharides supplementation on methanogenesis and energy and nitrogen utilization in dairy cows. Asian-Australas J Anim Sci 17(3): 349–54.
- Nakao M, Harada M, Kodama Y, Nakayama T, Shibano Y, Amachi T. 1994. Purification and characterization of a thermostable beta-galactosidase with high transgalactosylation activity from Saccharopolyspora rectivirgula. Appl Microbiol Biotechnol 40(5): 657–63.
- Nakayama T, Amachi T. 1999. Beta-galactosidase, enzymology. In: MC Flickinger, SW Drew, editors. Encyclopedia of bioprocess technology: fermentation, biocatalysis, and bioseparation. New York : John Wiley & Sons, Inc. p 1291–305.
- Nakkharat P, Haltrich D. 2006. Lactose hydrolysis and formation of galactooligosaccharides by a novel immobilized beta-galactosidase from the thermophilic fungus Talaromyces thermophilus. Appl Biochem Biotechnol 129(1–3): 215–25.
- Nakkharat P, Haltrich D. 2007. Beta-galactosidase from Talaromyces thermophilus immobilized on to Eupergit C for production of galacto-oligosaccharides during lactose hydrolysis in batch and packed-bed reactor. World J Microbiol Biotechnol 23(6): 759–64.
- Neri DFM, Balcao VM, Costa RS, Rocha I, Ferreira E, Torres DPM, Rodrigues LRM, Carvalho LB, Teixeira JA. 2009a. Galacto-oligosaccharides production during lactose hydrolysis by free Aspergillus oryzae beta-galactosidase and immobilized on magnetic polysiloxane-polyvinyl alcohol. Food Chem 115(1): 92–9.
- Neri DFM, Balcao VM, Dourado FOQ, Oliveira JMB, Carvalho LB, Teixeira JA. 2009b. Galactooligosaccharides production by beta-galactosidase immobilized onto magnetic polysiloxane-polyaniline particles. React Funct Polym 69(4): 246–51.
- Newburg DS. 2000. Oligosaccharides in human milk and bacterial colonization. J Pediatr Gastr Nutr 30: S8–17.
- Nguyen TH, Splechtna B, Krasteva S, Kneifel W, Kulbe KD, Divne C, Haltrich D. 2007. Characterization and molecular cloning of a heterodimeric beta-galactosidase from the probiotic strain Lactobacillus acidophilus R22. FEMS Microbiol Lett 269(1): 136–44.
- Nobre C, Santos MJ, Dominguez A, Torres D, Rocha O, Peres AM, Rocha I, Ferreira EC, Teixeira JA, Rodrigues LR. 2009. Comparison of adsorption equilibrium of fructose, glucose and sucrose on potassium gel-type and macroporous sodium ion-exchange resins. Anal Chim Acta 654(1): 71–6.
- Ohtsuka K, Tanoh A, Ozawa O, Kanematsu T, Uchida T, Shinke R. 1990a. Purification and properties of a beta-galactosidase with high galactosyl transfer activity from Cryptococcus laurentii OKN-4. J Ferment Bioengr 70(5): 301–7.
- Ohtsuka K, Tsuji K, Nakagawa Y, Ueda H, Ozawa O, Uchida T, Ichikawa T. 1990b. Availability of 4′-galactosyllactose (O-beta-D-galactopyranosyl-(1-4)-O-beta-D-galactopyranosyl-(1-4)-D-glucopyranose) in rat. J Nutr Sci Vitaminol 36(3): 265–76.
- Onishi N, Tanaka T. 1995. Purification and properties of a novel thermostable galacto-oligosaccharide-producing beta-galactosidase from Sterigmatomyces elviae CBS8119. Appl Environ Microbiol 61(11): 4026–30.
- Onishi N, Tanaka T. 1996. Purification and properties of a galacto- and gluco-oligosaccharide-producing beta-glycosidase from Rhodotorula minuta IFO879. J Ferment Bioengr 82(5): 439–43.
- Onishi N, Yokozeki K. 1996. Gluco-oligosaccharide and galacto-oligosaccharide production by Rhodotorula minuta IFO879. J Ferment Bioengr 82(2): 124–7.
- Onishi N, Tanaka T. 1997. Purification and characterization of galacto-oligosaccharide-producing beta-galactosidase from Sirobasidium magnum. Lett Appl Microbiol 24(2): 82–6.
- Onishi N, Yamashiro A, Yokozeki K. 1995. Production of galacto-oligosaccharide from lactose by Sterigmatomyces elviae CBS8119. Appl Environ Microbiol 61(11): 4022–5.
- Onishi N, Kira I, Yokozeki K. 1996. Galacto-oligosaccharide production from lactose by Sirobasidium magnum CBS6803. Lett Appl Microbiol 23(4): 253–6.
- Paige DM. 2005. Lactose intolerance. In: B Caballero, L Allen, A Prentice, editors. Encyclopedia of human nutrition. 2nd ed. Oxford : Elsevier Ltd. p 113–20.
10.1016/B0-12-226694-3/02175-X Google Scholar
- Panesar PS, Panesar R, Singh RS, Kennedy JF, Kumar H. 2006. Microbial production, immobilization and applications of beta-D-galactosidase. J Chem Technol Biotechnol 81(4): 530–43.
- Park HY, Kim HJ, Lee JK, Kim D, Oh DK. 2008. Galactooligosaccharide production by a thermostable beta-galactosidase from Sulfolobus solfataricus. World J Microbiol Biotechnol 24(8): 1553–8.
- Paterson AHJ. 2009. Production and uses of lactose. In: PLH McSweeney, PF Fox, editors. Lactose, water, salts and minor constituents. 3rd ed. New York : Springer. p 105–20.
- Pazur JH. 1953. The enzymatic conversion of lactose into galactosyl oligosaccharides. Science 117(3040): 355–6.
- Pazur JH, Tipton CL, Budovich T, Marsh JM. 1958. Structural characterization of products of enzymatic disproportionation of lactose. J Am Chem Soc 80(1): 119–21.
- Petzelbauer I, Reiter A, Splechtna B, Kosma P, Nidetzky B. 2000a. Transgalactosylation by thermostable beta-glycosidases from Pyrococcus furiosus and Sulfolobus solfataricus—binding interactions of nucleophiles with the galactosylated enzyme intermediate make major contributions to the formation of new beta-glycosides during lactose conversion. Eur J Biochem 267(16): 5055–66.
- Petzelbauer I, Zeleny R, Reiter A, Kulbe KD, Nidetzky B. 2000b. Development of an ultra-high-temperature process for the enzymatic hydrolysis of lactose: II. Oligosaccharide formation by two thermostable beta-glycosidases. Biotechnol Bioengr 69(2): 140–49.
10.1002/(SICI)1097-0290(20000720)69:2<140::AID-BIT3>3.0.CO;2-R CASPubMedWeb of Science®Google Scholar
- Petzelbauer I, Splechtna B, Nidetzky B. 2002. Development of an ultrahigh-temperature process for the enzymatic hydrolysis of lactose. III. Utilization of two thermostable beta-glycosidases in a continuous ultrafiltration membrane reactor and galacto-oligosaccharide formation under steady-state conditions. Biotechnol Bioengr 77(4): 394–404.
- Pivarnik LF, Senecal AG, Rand AG. 1995. Hydrolytic and transgalactosylic activities of commercial beta-galactosidase (lactase) in food processing. In: JE Kinsella, SL Taylor, editors. Advances in food and nutrition research. San Diego, Calif. : Academic Press Inc. p 1–102.
- Placier G, Watzlawick H, Rabiller C, Mattes R. 2009. Evolved beta-galactosidases from Geobacillus stearothermophilus with improved transgalactosylation yield for galacto-oligosaccharide production. Appl Environ Microbiol 75(19): 6312–21.
- Playne MJ, Crittenden RG. 2009. Galacto-oligosaccharides and other products derived from lactose. In: PLH McSweeney, PF Fox, editors. Lactose, water, salts and minor constituents. 3rd ed. New York : Springer. p 121–201.
10.1007/978-0-387-84865-5_5 Google Scholar
- Prakash BS, Suyama K, Itoh T, Adachi S. 1989. Structure elucidation of major galacto oligosaccharides formed by growing culture of Trichoderma harzianum. J Agric Food Chem 37(2): 334–7.
- Prakash S, Suyama K, Itoh T, Adachi S. 1987. Oligosaccharide formation by Trichoderma harzianum in lactose-containing medium. Biotechnol Lett 9(4): 249–52.
- Prapulla SG, Subhaprada V, Karanth NG. 2000. Microbial production of oligosaccharides: a review. Adv Appl Microbiol 47: 299–343.
- Prenosil JE, Stuker E, Bourne JR. 1987. Formation of oligosaccharides during enzymatic lactose hydrolysis and their importance in a whey hydrolysis process. 2. Experimental. Biotechnol Bioengr 30(9): 1026–31.
- Rabiu BA, Jay AJ, Gibson GR, Rastall RA. 2001. Synthesis and fermentation properties of novel galacto-oligosaccharides by beta-galactosidases from Bifidobacterium species. Appl Environ Microbiol 67(6): 2526–30.
- Rastall RA. 2006. Galacto-oligosaccharides as prebiotic food ingredients. In: GR Gibson, RA Rastall, editors. Prebiotics: development & application. West Sussex : John Wiley & Sons Ltd. p 101–9.
- Rehman SU. 2009. Reduced lactose and lactose-free dairy products. In: PLH McSweeney, PF Fox, editors. Lactose, water, salts and minor constituents. 3rd ed. New York : Springer. p 98–104.
- Richmond ML, Gray JI, Stine CM. 1981. Beta-galactosidase—review of recent research related to technological application, nutritional concerns, and immobilization. J Dairy Sci 64(9): 1759–71.
- Roberfroid M. 2007. Prebiotics: the concept revisited. J Nutr 137(3): 830S–7S.
- Roberfroid M, Gibson GR, Delzenne N. 1993. The biochemistry of oligofructose, a nondigestible fiber—an approach to calculate its caloric value. Nutr Rev 51(5): 137–46.
- Roberts HR, Pettinati JD. 1957. Oligosaccharide production—concentration effects in the enzymatic conversion of lactose to oligosaccharides. J Agric Food Chem 5(2): 130–4.
- Roos YH. 2009. Solid and liquid states of lactose. In: PLH McSweeney, PF Fox, editors. Lactose, water, salts and minor constituents. 3rd ed. New York : Springer. p 17–33.
- Ross RP, Mills S, Hill C, Fitzgerald GF, Stanton C. 2010. Specific metabolite production by gut microbiota as a basis for probiotic function. Int Dairy J 20(4): 269–76.
- Rowland IR, Tanaka R. 1993. The effects of transgalactosylated oligosaccharides on gut flora metabolism in rats associated with a human fecal microflora. J Appl Bacteriol 74(6): 667–74.
- Roy D, Daoudi L, Azaola A. 2002. Optimization of galacto-oligosaccharide production by Bifidobacterium infantis RW-8120 using response surface methodology. J Ind Microbiol Biotechnol 29(5): 281–5.
- Rustom IYS, Foda MI, Lopez-Leiva MH. 1998. Formation of oligosaccharides from whey UF-permeate by enzymatic hydrolysis—analysis of factors. Food Chem 62(2): 141–7.
- Sakai T, Tsuji H, Shibata S, Hayakawa K, Matsumoto K. 2008. Repeated-batch production of galactooligosaccharides from lactose at high concentration by using alginate-immobilized cells of Sporobolomyces singularis YIT 10047. J Gen Appl Microbiol 54(5): 285–93.
- Sako T, Matsumoto K, Tanaka R. 1999. Recent progress on research and applications of nondigestible galacto-oligosaccharides. Int Dairy J 9(1): 69–80.
- Santoso B, Mwenya B, Sar C, Gamo Y, Kobayashi T, Morikawa R, Kimura K, Mizukoshi H, Takahashi J. 2004. Effects of supplementing galacto-oligosaccharides, Yucca schidigera or nisin on rumen methanogenesis, nitrogen and energy metabolism in sheep. Livest Prod Sci 91(3): 209–17.
- Sar C, Santoso B, Mwenya B, Gamo Y, Kobayashi T, Morikawa R, Kimura K, Mizukoshi H, Takahashi J. 2004. Manipulation of rumen methanogenesis by the combination of nitrate with beta 1-4 galacto-oligosaccharides or nisin in sheep. Anim Feed Sci Technol 115(1–2): 129–42.
- Schaafsma G. 2008. Lactose and lactose derivatives as bioactive ingredients in human nutrition. Int Dairy J 18(5): 458–65.
- Sekirov I, Finlay BB. 2006. Human and microbe: united we stand. Nature Med 12(7): 736–7.
- Sheu DC, Li SY, Duan KJ, Chen CW. 1998. Production of galactooligosaccharides by beta-galactosidase immobilized on glutaraldehyde-treated chitosan beads. Biotechnol Technol 12(4): 273–6.
- Shin HJ, Yang JW. 1996. Galactooligosaccharide synthesis from lactose by Penicillium funiculosum cellulase. Biotechnol Lett 18(2): 143–4.
- Shin HJ, Park JM, Yang JW. 1998. Continuous production of galacto-oligosaccharides from lactose by Bullera singularis beta-galactosidase immobilized in chitosan beads. Process Biochem 33(8): 787–92.
- Silk DBA, Davis A, Vulevic J, Tzortzis G, Gibson GR. 2009. Clinical trial: the effects of a trans-galactooligosaccharide prebiotic on faecal microbiota and symptoms in irritable bowel syndrome. Aliment Pharmacol Ther 29(5): 508–18.
- Sinclair HR, De Slegte J, Gibson GR, Rastall RA. 2009. Galactooligosaccharides (GOS) inhibit Vibrio cholerae toxin binding to its GM1 receptor. J Agric Food Chem 57(8): 3113–9.
- Sinnott ML. 1990. Catalytic mechanisms of enzymatic glycosyl transfer. Chem Rev 90(7): 1171–202.
- Splechtna B, Petzelbauer I, Baminger U, Haltrich D, Kulbe KD, Nidetzky B. 2001. Production of a lactose-free galacto-oligosaccharide mixture by using selective enzymatic oxidation of lactose into lactobionic acid. Enzyme Microb Technol 29(6–7): 434–40.
- Splechtna B, Nguyen TH, Steinbock M, Kulbe KD, Lorenz W, Haltrich D. 2006. Production of prebiotic galacto-oligosaccharides from lactose using beta-galactosidases from Lactobacillus reuteri. J Agric Food Chem 54(14): 4999–5006.
- Splechtna B, Nguyen TH, Haltrich D. 2007. Comparison between discontinuous and continuous lactose conversion processes for the production of prebiotic galacto-oligosaccharides using beta-galactosidase from Lactobacillus reuteri. J Agric Food Chem 55(16): 6772–7.
- Stevenson DE, Stanley RA, Furneaux RH. 1996. Oligosaccharide and alkyl beta-galactopyranoside synthesis from lactose with Caldocellum saccharolyticum beta-glycosidase. Enzyme Microb Technol 18(8): 544–9.
- Tanaka R, Takayama H, Morotomi M, Kuroshima T, Ueyama S, Matsumoto K, Kuroda A, Mutai M. 1983. Effects of administration of TOS and Bifidbacterium breve 4006 on the human flora. Bifidobacteria Microflora 2: 17–24.
- Toba T, Adachi S. 1978. Hydrolysis of lactose by microbial beta-galactosidases—formation of oligosaccharides with special reference to 2-0-beta-D-galactopyranosyl-D-glucose. J Dairy Sci 61(1): 33–8.
- Toba T, Tomita Y, Itoh T, Adachi S. 1981. Beta-galactosidases of lactic-acid bacteria—characterization by oligosaccharides formed during hydrolysis of lactose. J Dairy Sci 64(2): 185–92.
- Toba T, Yokota A, Adachi S. 1985. Oligosaccharide structures formed during the hydrolysis of lactose by Aspergillus oryzae beta-galactosidase. Food Chem 16(2): 147–62.
- Tzortzis G. 2009. Functional properties of the second generation prebiotic Galacto-oligosaccharide (B-GOS). Agro Food Ind Hi Tec 20(3): 43–6.
- Tzortzis G, Vulevic J. 2009. Galacto-oligosaccharide prebiotics. In: D Charalampopoulos, RA Rastall, editors. Prebiotics and probiotics science and technology. New York : Springer. p 207–44.
10.1007/978-0-387-79058-9_7 Google Scholar
- Tzortzis G, Goulas AK, Gee JM, Gibson GR. 2005a. A novel galactooligosaccharide mixture increases the bifidobacterial population numbers in a continuous in vitro fermentation system and in the proximal colonic contents of pigs in vivo. J Nutr 135(7): 1726–31.
- Tzortzis G, Goulas AK, Gibson GR. 2005b. Synthesis of prebiotic galactooligosaccharides using whole cells of a novel strain, Bifidobacterium bifidum NCIMB 41171. Appl Microbiol Biotechnol 68(3): 412–6.
- Van Loo J, Cummings J, Delzenne N, Englyst H, Franck A, Hopkins M, Kok N, Macfarlane G, Newton D, Quigley M, Roberfroid M, Van Vliet T, Van Den Heuvel E. 1999. Functional food properties of non-digestible oligosaccharides: a consensus report from the ENDO project (DGXII AIRII-CT94-1095). Br J Nutr 81(2): 121–32.
- Vulevic J, Drakoularakou A, Yaqoob P, Tzortzis G, Gibson GR. 2008. Modulation of the fecal microflora profile and immune function by a novel trans-galactooligosaccharide mixture (B-GOS) in healthy elderly volunteers. Am J Clin Nutr 88(5): 1438–46.
- Wallenfels K. 1951. Enzymatische synthese von oligosacchariden aus disacchariden. Naturwissenschaften 38(13): 306–7.
- Wallenfels K, Malhotra OP. 1960. Beta-galactosidase. In: PD Boyer, editor. The enzymes. 2nd ed. New York : Academic Press Inc. p 409–30.
- Widmer F, Leuba JL. 1979. Beta-galactosidase from Aspergillus niger—separation and characterization of 3 multiple forms. Eur J Biochem 100(2): 559–67.
- Wikoff WR, Anfora AT, Liu J, Schultz PG, Lesley SA, Peters EC, Siuzdak G. 2009. Metabolomics analysis reveals large effects of gut microflora on mammalian blood metabolites. Proc Natl Acad Sci USA 106(10): 3698–703.
- Yanahira S, Kobayashi T, Suguri T, Nakakoshi M, Miura S, Ishikawa H, Nakajima I. 1995. Formation of oligosaccharides from lactose by Bacillus circulans beta-galactosidase. Biosci Biotechnol Biochem 59(6): 1021–6.
- Yang ST, Silva EM. 1995. Novel products and new technologies for use of a familiar carbohydrate, milk lactose. J Dairy Sci 78(11): 2541–62.
- Yang Y, Iji PA, Choct M. 2009. Dietary modulation of gut microflora in broiler chickens: a review of the role of six kinds of alternatives to in-feed antibiotics. World Poultry Sci J 65(1): 97–114.
- Zechel DL, Withers SG. 2001. Dissection of nucleophilic and acid-base catalysis in glycosidases. Curr Opin Chem Biol 5(6): 643–9.
- Zhou QZK, Chen XD, Li XM. 2003. Kinetics of lactose hydrolysis by beta-galactosidase of Kluyveromyces lactis immobilized on cotton fabric. Biotechnol Bioengr 81(2): 127–33.