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Mar. Drugs 2015, 13(2), 770-787; doi:10.3390/md13020770

Synthesis of the Oligosaccharides Related to Branching Sites of Fucosylated Chondroitin Sulfates from Sea Cucumbers

1
Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky prospect 47, 119991 Moscow B-334, Russia
2
Lomonosov Moscow State University, Leninskie gory, 119991 Moscow, Russia
*
Authors to whom correspondence should be addressed.
Academic Editor: Yoshihide Usami
Received: 1 December 2014 / Revised: 29 December 2014 / Accepted: 22 January 2015 / Published: 2 February 2015
(This article belongs to the Special Issue Synthesis around Marine Natural Products)
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Abstract

Natural anionic polysaccharides fucosylated chondroitin sulfates (FCS) from sea cucumbers attract great attention nowadays due to their ability to influence various biological processes, such as blood coagulation, thrombosis, angiogenesis, inflammation, bacterial and viral adhesion. To determine pharmacophore fragments in FCS we have started systematic synthesis of oligosaccharides with well-defined structure related to various fragments of these polysaccharides. In this communication, the synthesis of non-sulfated and selectively O-sulfated di- and trisaccharides structurally related to branching sites of FCS is described. The target compounds are built up of propyl β-d-glucuronic acid residue bearing at O-3 α-l-fucosyl or α-l-fucosyl-(1→3)-α-l-fucosyl substituents. O-Sulfation pattern in the fucose units of the synthetic targets was selected according to the known to date holothurian FCS structures. Stereospecific α-glycoside bond formation was achieved using 2-O-benzyl-3,4-di-O-chloroacetyl-α-l-fucosyl trichloroacetimidate as a donor. Stereochemical outcome of the glycosylation was explained by the remote participation of the chloroacetyl groups with the formation of the stabilized glycosyl cations, which could be attacked by the glycosyl acceptor only from the α-side. The experimental results were in good agreement with the SCF/MP2 calculated energies of such participation. The synthesized oligosaccharides are regarded as model compounds for the determination of a structure-activity relationship in FCS. View Full-Text
Keywords: fucosylated chondroitin sulfate; oligosaccharides; synthesis; glycosylation; stereoselectivity; remote participation; sulfation fucosylated chondroitin sulfate; oligosaccharides; synthesis; glycosylation; stereoselectivity; remote participation; sulfation
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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

Ustyuzhanina, N.E.; Fomitskaya, P.A.; Gerbst, A.G.; Dmitrenok, A.S.; Nifantiev, N.E. Synthesis of the Oligosaccharides Related to Branching Sites of Fucosylated Chondroitin Sulfates from Sea Cucumbers. Mar. Drugs 2015, 13, 770-787.

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