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Fluorous-assisted chemoenzymatic synthesis of heparan sulfate oligosaccharides. 2014
Chao Cai, and
Demetria M Dickinson, and
Lingyun Li, and
Sayaka Masuko, and
Matt Suflita, and
Victor Schultz, and
Shawn D Nelson, and
Ujjwal Bhaskar, and
Jian Liu, and
Robert J Linhardt
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.
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.
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