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Org Lett. 2014 Apr 18;16(8):2240-3. doi: 10.1021/ol500738g. Epub 2014 Apr 4.

Fluorous-assisted chemoenzymatic synthesis of heparan sulfate oligosaccharides.

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1
Department of Chemistry and Chemical Biology, ‡Department of Biology, and §Departments of Chemical and Biological Engineering and Biomedical Engineering, Center for Biotechnology and Interdisciplinary Studies, Rensselaer Polytechnic Institute , Troy, New York 12180, United States.

Abstract

The chemoenzymatic synthesis of heparan sulfate tetrasaccharide (1) and hexasaccharide (2) with a fluorous tag attached at the reducing end is reported. The fluorous tert-butyl dicarbonate ((F)Boc) tag did not interfere with enzymatic recognition for both elongation and specific sulfation, and flash purification was performed by standard fluorous solid-phase extraction (FSPE). Based on an (F)Boc attached disaccharide as acceptor, a series of partial N-sulfated, 6-O-sulfated heparan sulfate oligosaccharides were successfully synthesized employing fluorous techniques.

PMID:
24697306
PMCID:
PMC3998769
DOI:
10.1021/ol500738g
[Indexed for MEDLINE]
Free PMC Article
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