Abstract
A series of selectively sulfated di- and trisaccharide derivatives corresponding to the potential fragments of fucoidans with a α-(1 → 2)-linked fucobioside unit were synthesized and studied by 1Н and 13C NMR spectroscopy. NOE experiments and molecular modeling were used for a conformational analysis of the compounds synthesized. In the case of disaccharides, the experimental NOE values were found to agree with those obtained using modeling with the use of density functional theory (DFT) and differ from those resulting from modeling by the molecular mechanics MM3 force field. Trisaccharide fragments partially or completely sulfated in position 4 turned out to be correctly described by both MM3 force field and DFT computation.
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Gerbst, A.G., Grachev, A.A., Ustyuzhanina, N.E. et al. The Synthesis and NMR and Conformational Studies of Fucoidan Fragments: VI.1 Fragments with an α-(1 → 2)-Linked Fucobioside Unit. Russian Journal of Bioorganic Chemistry 30, 137–148 (2004). https://doi.org/10.1023/B:RUBI.0000023099.48598.9a
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DOI: https://doi.org/10.1023/B:RUBI.0000023099.48598.9a