A Simple Glycol Nucleic Acid
- Lilu Zhang
- ,
- Adam Peritz
- , and
- Eric Meggers
Abstract
A glycol nucleic acid (GNA) with an acyclic propylene glycol phosphodiester backbone forms stable antiparallel duplexes following the Watson−Crick base pairing rules.
*
In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.
Cited By
This article is cited by 255 publications.
- Pradeep S. Pallan, Terry P. Lybrand, Eriks Rozners, Mikhail Abramov, Guy Schepers, Elena Eremeeva, Piet Herdewijn, Martin Egli. Conformational Morphing by a DNA Analogue Featuring 7-Deazapurines and 5-Halogenpyrimidines and the Origins of Adenine-Tract Geometry. Biochemistry 2023, 62 (19) , 2854-2867. https://doi.org/10.1021/acs.biochem.3c00327
- Hikari Okita, Shuto Kondo, Keiji Murayama, Hiroyuki Asanuma. Rapid Chemical Ligation of DNA and Acyclic Threoninol Nucleic Acid (aTNA) for Effective Nonenzymatic Primer Extension. Journal of the American Chemical Society 2023, 145 (32) , 17872-17880. https://doi.org/10.1021/jacs.3c04979
- Giulia Iadevaia, Christopher A. Hunter. Recognition-Encoded Synthetic Information Molecules. Accounts of Chemical Research 2023, 56 (6) , 712-727. https://doi.org/10.1021/acs.accounts.3c00029
- Suchismita Rath, Biswajit Mohanty, Subhabrata Sen. “All-Aqueous” Tandem Boc-Deprotection and Alkylation of N-Bocbenzimidazole Derivatives under Visible Light with Alkyl Aryl Diazoacetates: Application to Site-Selective Insertion of Carbenes into the N–H Bond of Purines. The Journal of Organic Chemistry 2023, 88 (2) , 1036-1048. https://doi.org/10.1021/acs.joc.2c02467
- Tanushree Mana, Budhaditya Bhattacharya, Hiya Lahiri, Rupa Mukhopadhyay. XNAs: A Troubleshooter for Nucleic Acid Sensing. ACS Omega 2022, 7 (18) , 15296-15307. https://doi.org/10.1021/acsomega.2c00581
- Eric Largy, Alexander König, Anirban Ghosh, Debasmita Ghosh, Sanae Benabou, Frédéric Rosu, Valérie Gabelica. Mass Spectrometry of Nucleic Acid Noncovalent Complexes. Chemical Reviews 2022, 122 (8) , 7720-7839. https://doi.org/10.1021/acs.chemrev.1c00386
- Yanglingzhi Chen, Ryuya Nagao, Keiji Murayama, Hiroyuki Asanuma. Orthogonal Amplification Circuits Composed of Acyclic Nucleic Acids Enable RNA Detection. Journal of the American Chemical Society 2022, 144 (13) , 5887-5892. https://doi.org/10.1021/jacs.1c12659
- Trevor W. Manning, Abigail J. Van Riesen, Richard A. Manderville. Screening Internal Donor–Acceptor Biaryl Nucleobase Surrogates for Turn-On Fluorescence Affords an Aniline–Carboxythiophene Probe for Protein Detection by G-Quadruplex DNA. Bioconjugate Chemistry 2021, 32 (8) , 1791-1801. https://doi.org/10.1021/acs.bioconjchem.1c00270
- Li Wang, Shuai Huang, Meng Wang, Zhi-Yang Liu, Xu-Man Chen, Hong Yang. Synthesis and Self-Assembly of Alternating Heterodinucleoside Polytriazoles. Macromolecules 2021, 54 (1) , 341-350. https://doi.org/10.1021/acs.macromol.0c02276
- Micaela D. Gray, Prashant S. Deore, Andrew J. Chung, Abigail J. Van Riesen, Richard A. Manderville, Preethi Seelam Prabhakar, Stacey D. Wetmore. Lighting Up the Thrombin-Binding Aptamer G-Quadruplex with an Internal Cyanine-Indole-Quinolinium Nucleobase Surrogate. Direct Fluorescent Intensity Readout for Thrombin Binding without Topology Switching. Bioconjugate Chemistry 2020, 31 (11) , 2596-2606. https://doi.org/10.1021/acs.bioconjchem.0c00530
- Scott A. Sandford, Michel Nuevo, Partha P. Bera, Timothy J. Lee. Prebiotic Astrochemistry and the Formation of Molecules of Astrobiological Interest in Interstellar Clouds and Protostellar Disks. Chemical Reviews 2020, 120 (11) , 4616-4659. https://doi.org/10.1021/acs.chemrev.9b00560
- Michał Piotrowicz, Aleksandra Kowalczyk, Damian Trzybiński, Krzysztof Woźniak, Konrad Kowalski. Redox-Active Glycol Nucleic Acid (GNA) Components: Synthesis and Properties of the Ferrocenyl-GNA Nucleoside, Phosphoramidite, and Semicanonical Dinucleoside Phosphate. Organometallics 2020, 39 (6) , 813-823. https://doi.org/10.1021/acs.organomet.9b00851
- Henderson James Cleaves, II, Christopher Butch, Pieter Buys Burger, Jay Goodwin, Markus Meringer. One Among Millions: The Chemical Space of Nucleic Acid-Like Molecules. Journal of Chemical Information and Modeling 2019, 59 (10) , 4266-4277. https://doi.org/10.1021/acs.jcim.9b00632
- Min Luo, Elisabetta Groaz, Mathy Froeyen, Valérie Pezo, Faten Jaziri, Piotr Leonczak, Guy Schepers, Jef Rozenski, Philippe Marlière, Piet Herdewijn. Invading Escherichia coli Genetics with a Xenobiotic Nucleic Acid Carrying an Acyclic Phosphonate Backbone (ZNA). Journal of the American Chemical Society 2019, 141 (27) , 10844-10851. https://doi.org/10.1021/jacs.9b04714
- Hiya Lahiri, Sourav Mishra, Rupa Mukhopadhyay. Nanoscale Nucleic Acid Recognition at the Solid–Liquid Interface Using Xeno Nucleic Acid Probes. Langmuir 2019, 35 (27) , 8875-8888. https://doi.org/10.1021/acs.langmuir.8b02770
- Keiji Murayama, Yuuhei Yamano, Hiroyuki Asanuma. 8-Pyrenylvinyl Adenine Controls Reversible Duplex Formation between Serinol Nucleic Acid and RNA by [2 + 2] Photocycloaddition. Journal of the American Chemical Society 2019, 141 (24) , 9485-9489. https://doi.org/10.1021/jacs.9b03267
- Li Wang, Meng Wang, Ling-Xiang Guo, Ying Sun, Xue-Qin Zhang, Bao-Ping Lin, Hong Yang. Oligodeoxynucleosides with Olefin Bridges. Macromolecules 2019, 52 (2) , 649-659. https://doi.org/10.1021/acs.macromol.8b02115
- Xun Han, Dylan W. Domaille, Benjamin D. Fairbanks, Liangcan He, Heidi R. Culver, Xinpeng Zhang, Jennifer N. Cha, Christopher N. Bowman. New Generation of Clickable Nucleic Acids: Synthesis and Active Hybridization with DNA. Biomacromolecules 2018, 19 (10) , 4139-4146. https://doi.org/10.1021/acs.biomac.8b01164
- Jonathan A. Swain, Giulia Iadevaia, Christopher A. Hunter. H-Bonded Duplexes based on a Phenylacetylene Backbone. Journal of the American Chemical Society 2018, 140 (36) , 11526-11536. https://doi.org/10.1021/jacs.8b08087
- Lei Liang, Ming-Sheng Xie, Tao Qin, Man Zhu, Gui-Rong Qu, and Hai-Ming Guo . Regio- and Enantioselective Synthesis of Chiral Pyrimidine Acyclic Nucleosides via Rhodium-Catalyzed Asymmetric Allylation of Pyrimidines. Organic Letters 2017, 19 (19) , 5212-5215. https://doi.org/10.1021/acs.orglett.7b02482
- Alexander E. Stross, Giulia Iadevaia, Diego Núñez-Villanueva, and Christopher A. Hunter . Sequence-Selective Formation of Synthetic H-Bonded Duplexes. Journal of the American Chemical Society 2017, 139 (36) , 12655-12663. https://doi.org/10.1021/jacs.7b06619
- Koji Nakano, Junichi Tanabe, Ryoich Ishimatsu, and Toshihiko Imato . Monolithic Peptide–Nucleic Acid Hybrid Functioning as an Artificial Microperoxidase. Bioconjugate Chemistry 2017, 28 (8) , 2031-2034. https://doi.org/10.1021/acs.bioconjchem.7b00216
- Mark K. Schlegel, Donald J. Foster, Alexander V. Kel’in, Ivan Zlatev, Anna Bisbe, Muthusamy Jayaraman, Jeremy G. Lackey, Kallanthottathil G. Rajeev, Klaus Charissé, Joel Harp, Pradeep S. Pallan, Martin A. Maier, Martin Egli, and Muthiah Manoharan . Chirality Dependent Potency Enhancement and Structural Impact of Glycol Nucleic Acid Modification on siRNA. Journal of the American Chemical Society 2017, 139 (25) , 8537-8546. https://doi.org/10.1021/jacs.7b02694
- Abhishek Singhal, Valentina Bagnacani, Roberto Corradini, and Peter E. Nielsen . Toward Peptide Nucleic Acid (PNA) Directed Peptide Translation Using Ester Based Aminoacyl Transfer. ACS Chemical Biology 2014, 9 (11) , 2612-2620. https://doi.org/10.1021/cb5005349
- Vanesa Vaquero-Vara, Di Zhang, Brian C. Dian, David W. Pratt, and Timothy S. Zwier . Delicate Balance of Hydrogen Bonding Forces in d-Threoninol. The Journal of Physical Chemistry A 2014, 118 (35) , 7267-7273. https://doi.org/10.1021/jp410859n
- RuoWen Wang, Guizhi Zhu, Lei Mei, Yan Xie, Haibin Ma, Mao Ye, Feng-Ling Qing, and Weihong Tan . Automated Modular Synthesis of Aptamer–Drug Conjugates for Targeted Drug Delivery. Journal of the American Chemical Society 2014, 136 (7) , 2731-2734. https://doi.org/10.1021/ja4117395
- Tao Wei, Ming-Sheng Xie, Gui-Rong Qu, Hong-Ying Niu, and Hai-Ming Guo . A New Strategy To Construct Acyclic Nucleosides via Ag(I)-Catalyzed Addition of Pronucleophiles to 9-Allenyl-9H-purines. Organic Letters 2014, 16 (3) , 900-903. https://doi.org/10.1021/ol4036566
- Joel R. Morgan, David V. X. Nguyen, Angela R. Frohman, Sara R. Rybka, and John A. Zebala . Reversible Metal-Dependent Destabilization and Stabilization of a Stem-Chelate-Loop Probe Binding to an Unmodified DNA Target. Bioconjugate Chemistry 2012, 23 (10) , 2020-2024. https://doi.org/10.1021/bc3003293
- Emil Wierzbinski, Arnie de Leon, Xing Yin, Alexander Balaeff, Kathryn L. Davis, Srinivas Reppireddy, Ravindra Venkatramani, Shahar Keinan, Danith H. Ly, Marcela Madrid, David N. Beratan, Catalina Achim, and David H. Waldeck . Effect of Backbone Flexibility on Charge Transfer Rates in Peptide Nucleic Acid Duplexes. Journal of the American Chemical Society 2012, 134 (22) , 9335-9342. https://doi.org/10.1021/ja301677z
- Andrew T. Johnson, Mark K. Schlegel, Eric Meggers, Lars-Oliver Essen, and Olaf Wiest . On the Structure and Dynamics of Duplex GNA. The Journal of Organic Chemistry 2011, 76 (19) , 7964-7974. https://doi.org/10.1021/jo201469b
- Hiroyuki Asanuma, Takasuke Toda, Keiji Murayama, Xingguo Liang, and Hiromu Kashida . Unexpectedly Stable Artificial Duplex from Flexible Acyclic Threoninol. Journal of the American Chemical Society 2010, 132 (42) , 14702-14703. https://doi.org/10.1021/ja105539u
- Eric Meggers and Lilu Zhang. Synthesis and Properties of the Simplified Nucleic Acid Glycol Nucleic Acid. Accounts of Chemical Research 2010, 43 (8) , 1092-1102. https://doi.org/10.1021/ar900292q
- Robert Häner, Florian Garo, Daniel Wenger and Vladimir L. Malinovskii. Oligopyrenotides: Abiotic, Polyanionic Oligomers with Nucleic Acid-like Structural Properties. Journal of the American Chemical Society 2010, 132 (21) , 7466-7471. https://doi.org/10.1021/ja102042p
- Filbert Totsingan, Vipul Jain, W. Clay Bracken, Andrea Faccini, Tullia Tedeschi, Rosangela Marchelli, Roberto Corradini, Neville R. Kallenbach and Mark M. Green . Conformational Heterogeneity in PNA:PNA Duplexes. Macromolecules 2010, 43 (6) , 2692-2703. https://doi.org/10.1021/ma902797f
- Jan Štambaský, Michal Hocek and Pavel Kočovský. C-Nucleosides: Synthetic Strategies and Biological Applications. Chemical Reviews 2009, 109 (12) , 6729-6764. https://doi.org/10.1021/cr9002165
- Sanchita Biswas, Kevin D. Belfield, Ritesh K. Das, Siddhartha Ghosh and Arthur F. Hebard . Block Copolymer-Mediated Formation of Superparamagnetic Nanocomposites. Chemistry of Materials 2009, 21 (23) , 5644-5653. https://doi.org/10.1021/cm902854d
- Mark K. Schlegel and Eric Meggers. Improved Phosphoramidite Building Blocks for the Synthesis of the Simplified Nucleic Acid GNA. The Journal of Organic Chemistry 2009, 74 (12) , 4615-4618. https://doi.org/10.1021/jo900365a
- Harleen Kaur, Amit Arora, K. Gogoi, P. Solanke, Anita D. Gunjal, Vaijayanti A. Kumar and Souvik Maiti. Effects for the Incorporation of Five-atom Thioacetamido Nucleic Acid (TANA) Backbone on Hybridization Thermodynamics and Kinetics of DNA Duplexes. The Journal of Physical Chemistry B 2009, 113 (9) , 2944-2951. https://doi.org/10.1021/jp808747g
- Jesse J. Chen, Xin Cai and Jack W. Szostak . N2′→P3′ Phosphoramidate Glycerol Nucleic Acid as a Potential Alternative Genetic System. Journal of the American Chemical Society 2009, 131 (6) , 2119-2121. https://doi.org/10.1021/ja809069b
- Marc-Olivier Ebert, Christian Mang, Ramanarayanan Krishnamurthy, Albert Eschenmoser and Bernhard Jaun. The Structure of a TNA−TNA Complex in Solution: NMR Study of the Octamer Duplex Derived from α-(l)-Threofuranosyl-(3′-2′)-CGAATTCG. Journal of the American Chemical Society 2008, 130 (45) , 15105-15115. https://doi.org/10.1021/ja8041959
- Jhimli Sengupta and Anup Bhattacharjya. Synthesis of Ether-Linked Oligoribo- and Xylonucleosides from 3,5′-Ether-Linked Pseudosaccharides. The Journal of Organic Chemistry 2008, 73 (17) , 6860-6863. https://doi.org/10.1021/jo8007429
- Yasuhiro Doi, Junya Chiba, Tomoyuki Morikawa and Masahiko Inouye. Artificial DNA Made Exclusively of Nonnatural C-Nucleosides with Four Types of Nonnatural Bases. Journal of the American Chemical Society 2008, 130 (27) , 8762-8768. https://doi.org/10.1021/ja801058h
- Mark K. Schlegel, Lars-Oliver Essen and Eric Meggers. Duplex Structure of a Minimal Nucleic Acid. Journal of the American Chemical Society 2008, 130 (26) , 8158-8159. https://doi.org/10.1021/ja802788g
- Richard S. Zhang, Elizabeth O. McCullum and John C. Chaput. Synthesis of Two Mirror Image 4-Helix Junctions Derived from Glycerol Nucleic Acid. Journal of the American Chemical Society 2008, 130 (18) , 5846-5847. https://doi.org/10.1021/ja800079j
- Allen T. Horhota, Jack W. Szostak, and Larry W. McLaughlin . Glycerol Nucleoside Triphosphates: Synthesis and Polymerase Substrate Activities. Organic Letters 2006, 8 (23) , 5345-5347. https://doi.org/10.1021/ol062232u
- Pradeep S. Pallan,, Peter von Matt,, Christopher J. Wilds,, Karl-Heinz Altmann, and, Martin Egli. RNA-Binding Affinities and Crystal Structure of Oligonucleotides Containing Five-Atom Amide-Based Backbone Structures,. Biochemistry 2006, 45 (26) , 8048-8057. https://doi.org/10.1021/bi060354o
- Saman Alavi. Simple Ethers as Models of Sugar Molecules in Calculations of Vertical Excitation Energies of DNA and RNA Nucleosides. The Journal of Physical Chemistry A 2005, 109 (42) , 9536-9541. https://doi.org/10.1021/jp052238l
- Siddhant Sethi, Hailili Zumila, Yasuha Watanabe, Junling Mo, Kenzo Fujimoto. UltraFast PhotoInduced double duplex DNA invasion into a 400-mer dsDNA target. Bioorganic & Medicinal Chemistry Letters 2024, 98 , 129597. https://doi.org/10.1016/j.bmcl.2023.129597
- Konrad Kowalski. Synthesis and chemical transformations of glycol nucleic acid (GNA) nucleosides. Bioorganic Chemistry 2023, 141 , 106921. https://doi.org/10.1016/j.bioorg.2023.106921
- Divita Mathur, Sebastián A. Díaz, Niko Hildebrandt, Ryan D. Pensack, Bernard Yurke, Austin Biaggne, Lan Li, Joseph S. Melinger, Mario G. Ancona, William B. Knowlton, Igor L. Medintz. Pursuing excitonic energy transfer with programmable DNA-based optical breadboards. Chemical Society Reviews 2023, 52 (22) , 7848-7948. https://doi.org/10.1039/D0CS00936A
- Keiji Murayama, Hikari Okita, Hiroyuki Asanuma. Highly Functional Acyclic Xeno Nucleic Acids. Bulletin of the Chemical Society of Japan 2023, 96 (10) , 1179-1187. https://doi.org/10.1246/bcsj.20230188
- Daniele Rosa-Gastaldo, Andrea Dalla Valle, Tommaso Marchetti, Luca Gabrielli. Sequence-selective duplex formation and template effect in recognition-encoded oligoanilines. Chemical Science 2023, 14 (33) , 8878-8888. https://doi.org/10.1039/D3SC00880K
- Yusuke Kawamoto, You Wu, Yuki Takahashi, Yoshinobu Takakura. Development of nucleic acid medicines based on chemical technology. Advanced Drug Delivery Reviews 2023, 199 , 114872. https://doi.org/10.1016/j.addr.2023.114872
- Martin Egli, Mark K. Schlegel, Muthiah Manoharan. Acyclic ( S )-glycol nucleic acid ( S -GNA) modification of siRNAs improves the safety of RNAi therapeutics while maintaining potency. RNA 2023, 29 (4) , 402-414. https://doi.org/10.1261/rna.079526.122
- Anna Graczyk, Ewa Radzikowska-Cieciura, Renata Kaczmarek, Roza Pawlowska, Arkadiusz Chworos. Modified Nucleotides for Chemical and Enzymatic Synthesis of Therapeutic RNA. Current Medicinal Chemistry 2023, 30 (11) , 1320-1347. https://doi.org/10.2174/0929867330666221014111403
- Guilherme Pavão, Isabela Sfalcin, Diego Bonatto. Biocontainment Techniques and Applications for Yeast Biotechnology. Fermentation 2023, 9 (4) , 341. https://doi.org/10.3390/fermentation9040341
- Hermann Neitz, Irene Bessi, Valentin Kachler, Manuela Michel, Claudia Höbartner. Tailored Tolane‐Perfluorotolane Assembly as Supramolecular Base Pair Replacement in DNA. Angewandte Chemie 2023, 135 (1) https://doi.org/10.1002/ange.202214456
- Hermann Neitz, Irene Bessi, Valentin Kachler, Manuela Michel, Claudia Höbartner. Tailored Tolane‐Perfluorotolane Assembly as Supramolecular Base Pair Replacement in DNA. Angewandte Chemie International Edition 2023, 62 (1) https://doi.org/10.1002/anie.202214456
- Hui-Ting Lee, Alexander Lushnikov, Luis A. Marky. Interaction of Poly(Ethylene Glycol)-b-Poly-L-Lysine Copolymers with DNA Structures: A Thermodynamic Investigation. 2023, 1-22. https://doi.org/10.1007/978-981-16-1313-5_35-1
- Hui-Ting Lee, Alexander Lushnikov, Luis A. Marky. Interaction of Poly(Ethylene Glycol)-b-Poly-L-Lysine Copolymers with DNA Structures: A Thermodynamic Investigation. 2023, 995-1016. https://doi.org/10.1007/978-981-19-9776-1_35
- Klaus Paschek, Dmitry A. Semenov, Ben K. D. Pearce, Kevin Lange, Thomas K. Henning, Ralph E. Pudritz. Meteorites and the RNA World: Synthesis of Nucleobases in Carbonaceous Planetesimals and the Role of Initial Volatile Content. The Astrophysical Journal 2023, 942 (1) , 50. https://doi.org/10.3847/1538-4357/aca27e
- Gleb S. Ivanov, Vyacheslav G. Tribulovich, Nikolay B. Pestov, Temitope I. David, Abdul-Saleem Amoah, Tatyana V. Korneenko, Nikolai A. Barlev. Artificial genetic polymers against human pathologies. Biology Direct 2022, 17 (1) https://doi.org/10.1186/s13062-022-00353-7
- Yifan Guo, Lianwei Li, Jinxian Yang. Intrachain and interchain complexation of polyacrylic acids bottlebrush chains with Ca2+ in aqueous solutions. Polymer 2022, 260 , 125353. https://doi.org/10.1016/j.polymer.2022.125353
- Yongshu Li, Bihui Huang, Zhichao Xue, Yunhua Gao, Zhenjian Zhuo. Nucleic acid therapy in pediatric cancer. Pharmacological Research 2022, 184 , 106441. https://doi.org/10.1016/j.phrs.2022.106441
- Kirk M. Brown, Jayaprakash K. Nair, Maja M. Janas, Yesseinia I. Anglero-Rodriguez, Lan T. H. Dang, Haiyan Peng, Christopher S. Theile, Elena Castellanos-Rizaldos, Christopher Brown, Donald Foster, Jeffrey Kurz, Jeffrey Allen, Rajanikanth Maganti, Jing Li, Shigeo Matsuda, Matthew Stricos, Tyler Chickering, Michelle Jung, Kelly Wassarman, Jeff Rollins, Lauren Woods, Alex Kelin, Dale C. Guenther, Melissa W. Mobley, John Petrulis, Robin McDougall, Timothy Racie, Jessica Bombardier, Diana Cha, Saket Agarwal, Lei Johnson, Yongfeng Jiang, Scott Lentini, Jason Gilbert, Tuyen Nguyen, Samantha Chigas, Sarah LeBlanc, Urjana Poreci, Anne Kasper, Arlin B. Rogers, Saeho Chong, Wendell Davis, Jessica E. Sutherland, Adam Castoreno, Stuart Milstein, Mark K. Schlegel, Ivan Zlatev, Klaus Charisse, Mark Keating, Muthiah Manoharan, Kevin Fitzgerald, Jing-Tao Wu, Martin A. Maier, Vasant Jadhav. Expanding RNAi therapeutics to extrahepatic tissues with lipophilic conjugates. Nature Biotechnology 2022, 40 (10) , 1500-1508. https://doi.org/10.1038/s41587-022-01334-x
- Aleksandra Kowalczyk, Michał Piotrowicz, Magdalena Gapińska, Damian Trzybiński, Krzysztof Woźniak, Taryn M. Golding, Tameryn Stringer, Gregory S. Smith, Rafał Czerwieniec, Konrad Kowalski. Chemistry of glycol nucleic acid (GNA): Synthesis, photophysical characterization and insight into the biological activity of phenanthrenyl GNA constituents. Bioorganic Chemistry 2022, 125 , 105847. https://doi.org/10.1016/j.bioorg.2022.105847
- Mark K Schlegel, Maja M Janas, Yongfeng Jiang, Joseph D Barry, Wendell Davis, Saket Agarwal, Daniel Berman, Christopher R Brown, Adam Castoreno, Sarah LeBlanc, Abigail Liebow, Tara Mayo, Stuart Milstein, Tuyen Nguyen, Svetlana Shulga-Morskaya, Sarah Hyde, Sally Schofield, John Szeto, Lauren Blair Woods, Vedat O Yilmaz, Muthiah Manoharan, Martin Egli, Klaus Charissé, Laura Sepp-Lorenzino, Patrick Haslett, Kevin Fitzgerald, Vasant Jadhav, Martin A Maier. From bench to bedside: Improving the clinical safety of GalNAc–siRNA conjugates using seed-pairing destabilization. Nucleic Acids Research 2022, 50 (12) , 6656-6670. https://doi.org/10.1093/nar/gkac539
- Jonathan K. Watts. Nucleic Acid Therapeutics. 2022, 350-402. https://doi.org/10.1039/9781837671328-00350
- Keiji Murayama, Hiromu Kashida, Hiroyuki Asanuma. Methyl group configuration on acyclic threoninol nucleic acids ( a TNAs) impacts supramolecular properties. Organic & Biomolecular Chemistry 2022, 20 (20) , 4115-4122. https://doi.org/10.1039/D2OB00266C
- Yuichiro Aiba, Masanari Shibata, Osami Shoji. Sequence-Specific Recognition of Double-Stranded DNA by Peptide Nucleic Acid Forming Double-Duplex Invasion Complex. Applied Sciences 2022, 12 (7) , 3677. https://doi.org/10.3390/app12073677
- Hiroyuki Asanuma, Yukiko Kamiya, Hiromu Kashida, Keiji Murayama. Xeno nucleic acids (XNAs) having non-ribose scaffolds with unique supramolecular properties. Chemical Communications 2022, 58 (25) , 3993-4004. https://doi.org/10.1039/D1CC05868A
- Akinori Kuzuya. Molecular Material for Molecular Robots. 2022, 215-245. https://doi.org/10.1007/978-981-19-3987-7_6
- Keiji Murayama, Hikari Okita, Takumi Kuriki, Hiroyuki Asanuma. Nonenzymatic polymerase-like template-directed synthesis of acyclic l-threoninol nucleic acid. Nature Communications 2021, 12 (1) https://doi.org/10.1038/s41467-021-21128-0
- Agnieszka Tomaszewska-Antczak, Piotr Guga. Acyclic Nucleic Acids with Phosphodiester Linkages—Synthesis, Properties and Potential Applications. Applied Sciences 2021, 11 (24) , 12125. https://doi.org/10.3390/app112412125
- Mark K Schlegel, Shigeo Matsuda, Christopher R Brown, Joel M Harp, Joseph D Barry, Daniel Berman, Adam Castoreno, Sally Schofield, John Szeto, Muthiah Manoharan, Klaus Charissé, Martin Egli, Martin A Maier. Overcoming GNA/RNA base-pairing limitations using isonucleotides improves the pharmacodynamic activity of ESC+ GalNAc-siRNAs. Nucleic Acids Research 2021, 49 (19) , 10851-10867. https://doi.org/10.1093/nar/gkab916
- Keiji Murayama, Hiroyuki Asanuma. Design and Hybridization Properties of Acyclic Xeno Nucleic Acid Oligomers. ChemBioChem 2021, 22 (15) , 2507-2515. https://doi.org/10.1002/cbic.202100184
- Joanna Skiba, Aleksandra Kowalczyk, Damian Trzybiński, Krzysztof Woźniak, Valerije Vrček, Magdalena Gapińska, Konrad Kowalski. Stereo‐Defined Ferrocenyl Glycol Nucleic Acid (Fc‐GNA) Constituents: Synthesis, Electrochemistry, Mechanism of Formation, and Anticancer Activity Studies. European Journal of Inorganic Chemistry 2021, 2021 (22) , 2171-2181. https://doi.org/10.1002/ejic.202100193
- Syed Azmal Ali, Deepti Mittal, Gurjeet Kaur. In-situ monitoring of xenobiotics using genetically engineered whole-cell-based microbial biosensors: recent advances and outlook. World Journal of Microbiology and Biotechnology 2021, 37 (5) https://doi.org/10.1007/s11274-021-03024-3
- Luke K. McKenzie, Roberto El-Khoury, James D. Thorpe, Masad J. Damha, Marcel Hollenstein. Recent progress in non-native nucleic acid modifications. Chemical Society Reviews 2021, 50 (8) , 5126-5164. https://doi.org/10.1039/D0CS01430C
- Marie Flamme, Chiara Figazzolo, Gilles Gasser, Marcel Hollenstein. Enzymatic construction of metal-mediated nucleic acid base pairs. Metallomics 2021, 13 (4) https://doi.org/10.1093/mtomcs/mfab016
- Resat Aksakal, Chiel Mertens, Matthieu Soete, Nezha Badi, Filip Du Prez. Applications of Discrete Synthetic Macromolecules in Life and Materials Science: Recent and Future Trends. Advanced Science 2021, 8 (6) https://doi.org/10.1002/advs.202004038
- Asem Alenaizan, Joshua L Barnett, Nicholas V Hud, C David Sherrill, Anton S Petrov. The proto-Nucleic Acid Builder: a software tool for constructing nucleic acid analogs. Nucleic Acids Research 2021, 49 (1) , 79-89. https://doi.org/10.1093/nar/gkaa1159
- Shilpa R. Rao, Shelby L. Schettler, W. Seth Horne. Metal‐Binding Foldamers. ChemPlusChem 2021, 86 (1) , 137-145. https://doi.org/10.1002/cplu.202000730
- Chandrasekar Selvaraj, Srinivas B.T.V, Hai Xiong. Developing Trends in DNA Biosensor and Their Applications. 2021, 245-284. https://doi.org/10.1007/978-3-030-63791-0_8
- Claudia Riccardi, Ettore Napolitano, Chiara Platella, Domenica Musumeci, Daniela Montesarchio. G-quadruplex-based aptamers targeting human thrombin: Discovery, chemical modifications and antithrombotic effects. Pharmacology & Therapeutics 2021, 217 , 107649. https://doi.org/10.1016/j.pharmthera.2020.107649
- Christopher Liczner, Kieran Duke, Gabrielle Juneau, Martin Egli, Christopher J Wilds. Beyond ribose and phosphate: Selected nucleic acid modifications for structure–function investigations and therapeutic applications. Beilstein Journal of Organic Chemistry 2021, 17 , 908-931. https://doi.org/10.3762/bjoc.17.76
- Samuel C. Leguizamon, Timothy F. Scott. Sequence-selective dynamic covalent assembly of information-bearing oligomers. Nature Communications 2020, 11 (1) https://doi.org/10.1038/s41467-020-14607-3
- Yukiko Kamiya, Tadashi Satoh, Atsuji Kodama, Tatsuya Suzuki, Keiji Murayama, Hiromu Kashida, Susumu Uchiyama, Koichi Kato, Hiroyuki Asanuma. Intrastrand backbone-nucleobase interactions stabilize unwound right-handed helical structures of heteroduplexes of L-aTNA/RNA and SNA/RNA. Communications Chemistry 2020, 3 (1) https://doi.org/10.1038/s42004-020-00400-2
- Masatoshi Sunaga, Dai Motegi, Yuya Motegi, Kazuo Shinozuka, Tomohisa Moriguchi. Systematic Evaluation of Hybridization Property and Photo-Crosslinking Ability of Modified Oligonucleotides Containing Benzophenone-Bearing Glycol Nucleoside Analogs. Advanced Engineering Forum 2020, 38 , 57-62. https://doi.org/10.4028/www.scientific.net/AEF.38.57
- Kasper M. Beck, Marie B. Krogh, Mick Hornum, Paul T. Ludford, Yitzhak Tor, Poul Nielsen. Double-headed nucleotides as xeno nucleic acids: information storage and polymerase recognition. Organic & Biomolecular Chemistry 2020, 18 (36) , 7213-7223. https://doi.org/10.1039/D0OB01426E
- Peng Nie, Yanfen Bai, Hui Mei. Synthetic Life with Alternative Nucleic Acids as Genetic Materials. Molecules 2020, 25 (15) , 3483. https://doi.org/10.3390/molecules25153483
- Luca Gabrielli, Christopher A. Hunter. Supramolecular catalysis by recognition-encoded oligomers: discovery of a synthetic imine polymerase. Chemical Science 2020, 11 (28) , 7408-7414. https://doi.org/10.1039/D0SC02234A
- Masaki Hibino, Yuichiro Aiba, Osami Shoji. Cationic guanine: positively charged nucleobase with improved DNA affinity inhibits self-duplex formation. Chemical Communications 2020, 56 (17) , 2546-2549. https://doi.org/10.1039/D0CC00169D
- Philip M. Punt, Lukas M. Stratmann, Sinem Sevim, Lena Knauer, Carsten Strohmann, Guido H. Clever. Heteroleptic Coordination Environments in Metal-Mediated DNA G-Quadruplexes. Frontiers in Chemistry 2020, 8 https://doi.org/10.3389/fchem.2020.00026
- Keiji Murayama, Hiroyuki Asanuma. A Quencher‐Free Linear Probe from Serinol Nucleic Acid with a Fluorescent Uracil Analogue. ChemBioChem 2020, 21 (1-2) , 120-128. https://doi.org/10.1002/cbic.201900498
- Luca Gabrielli, Diego Núñez-Villanueva, Christopher A. Hunter. Two-component assembly of recognition-encoded oligomers that form stable H-bonded duplexes. Chemical Science 2020, 11 (2) , 561-566. https://doi.org/10.1039/C9SC04250D
- Kim A. Lennox, Mark A. Behlke. Chemical Modifications in RNA Interference and CRISPR/Cas Genome Editing Reagents. 2020, 23-55. https://doi.org/10.1007/978-1-0716-0290-4_2
- Vivek K. Sharma, Balaji Olety, Ashok K. Prasad. N-acetylgalactosamine (GalNAc)-conjugates: Delivering oligonucleotide drugs to the liver. 2020, 641-667. https://doi.org/10.1016/B978-0-12-816675-8.00016-6
- Hidenori Okamura, Antony Crisp, Sarah Hübner, Sidney Becker, Petra Rovó, Thomas Carell. Proto‐Urea‐RNA (Wöhler RNA) Containing Unusually Stable Urea Nucleosides. Angewandte Chemie 2019, 131 (51) , 18864-18869. https://doi.org/10.1002/ange.201911746
- Hidenori Okamura, Antony Crisp, Sarah Hübner, Sidney Becker, Petra Rovó, Thomas Carell. Proto‐Urea‐RNA (Wöhler RNA) Containing Unusually Stable Urea Nucleosides. Angewandte Chemie International Edition 2019, 58 (51) , 18691-18696. https://doi.org/10.1002/anie.201911746