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Mar. Drugs 2015, 13(2), 936-947; doi:10.3390/md13020936

Conformational Analysis of the Oligosaccharides Related to Side Chains of Holothurian Fucosylated Chondroitin Sulfates

N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky prospect 47, 119991 Moscow B-334, Russia
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Academic Editor: Paola Laurienzo
Received: 8 December 2014 / Accepted: 3 February 2015 / Published: 12 February 2015
(This article belongs to the Collection Marine Polysaccharides)
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Abstract

Anionic polysaccharides fucosylated chondroitin sulfates (FCS) from holothurian species were shown to affect various biological processes, such as metastasis, angiogenesis, clot formation, thrombosis, inflammation, and some others. To understand the mechanism of FCSs action, knowledge about their spatial arrangement is required. We have started the systematic synthesis, conformational analysis, and study of biological activity of the oligosaccharides related to various fragments of these types of natural polysaccharides. In this communication, five molecules representing distinct structural fragments of chondroitin sulfate have been studied by means of molecular modeling and NMR. These are three disaccharides and two trisaccharides containing fucose and glucuronic acid residues with one sulfate group per each fucose residue or without it. Long-range C–H coupling constants were used for the verification of the theoretical models. The presence of two conformers for both linkage types was revealed. For the Fuc–GlA linkage, the dominant conformer was the same as described previously in a literature as the molecular dynamics (MD) average in a dodechasaccharide FCS fragment representing the backbone chain of the polysaccharide including GalNAc residues. This shows that the studied oligosaccharides, in addition to larger ones, may be considered as reliable models for Quantitative Structure-Activity Relationship (QSAR) studies to reveal pharmacophore fragments of FCS. View Full-Text
Keywords: fucosylated chondroitin sulfate; oligosaccharides; conformational analysis; glycosidic linkage; Karplus equation; long range C–H coupling constants fucosylated chondroitin sulfate; oligosaccharides; conformational analysis; glycosidic linkage; Karplus equation; long range C–H coupling constants
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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MDPI and ACS Style

Gerbst, A.G.; Dmitrenok, A.S.; Ustyuzhanina, N.E.; Nifantiev, N.E. Conformational Analysis of the Oligosaccharides Related to Side Chains of Holothurian Fucosylated Chondroitin Sulfates. Mar. Drugs 2015, 13, 936-947.

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