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Divergent heparin oligosaccharide synthesis with preinstalled sulfate esters.

ABSTRACT: Traditional chemical synthesis of heparin oligosaccharides first involves assembly of the full length oligosaccharide backbone followed by sulfation. Herein, we report an alternative strategy in which the O-sulfate was introduced onto glycosyl building blocks as a trichloroethyl ester prior to assembly of the full length oligosaccharide. This allowed divergent preparation of both sulfated and non-sulfated building blocks from common advanced intermediates. The O-sulfate esters were found to be stable during glycosylation as well as typical synthetic manipulations encountered during heparin oligosaccharide synthesis. Furthermore, the presence of sulfate esters in both glycosyl donors and acceptors did not adversely affect the glycosylation yields, which enabled us to assemble multiple heparin oligosaccharides with preinstalled 6-O-sulfates.

SUBMITTER: Tiruchinapally G

PROVIDER: S-EPMC3324038 | biostudies-literature | 2011 Aug

REPOSITORIES: biostudies-literature

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Divergent heparin oligosaccharide synthesis with preinstalled sulfate esters.

Tiruchinapally Gopinath G Yin Zhaojun Z El-Dakdouki Mohammad M Wang Zhen Z Huang Xuefei X

Chemistry (Weinheim an der Bergstrasse, Germany) 20110722 36

Traditional chemical synthesis of heparin oligosaccharides first involves assembly of the full length oligosaccharide backbone followed by sulfation. Herein, we report an alternative strategy in which the O-sulfate was introduced onto glycosyl building blocks as a trichloroethyl ester prior to assembly of the full length oligosaccharide. This allowed divergent preparation of both sulfated and non-sulfated building blocks from common advanced intermediates. The O-sulfate esters were found to be s ...[more]

PMID: 21786352

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