Fluorous-Assisted Chemoenzymatic Synthesis of Heparan Sulfate Oligosaccharides | Zendy

Chao Cai | Zendy; Demetria M. Dickinson | Zendy; Lingyun Li | Zendy; Sayaka Masuko | Zendy; Matt Suflita | Zendy; Victor Schultz | Zendy; Shawn D. Nelson | Zendy; Ujjwal Bhaskar | Zendy; Jian Liu | Zendy; Robert J. Linhardt | Zendy

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Fluorous-Assisted Chemoenzymatic Synthesis of Heparan Sulfate Oligosaccharides

Author(s) -

Chao Cai,

Demetria M. Dickinson,

Lingyun Li,

Sayaka Masuko,

Matt Suflita,

Victor Schultz,

Shawn D. Nelson,

Ujjwal Bhaskar,

Jian Liu,

Robert J. Linhardt

Publication year - 2014

Publication title -

organic letters

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.94

H-Index - 239

eISSN - 1523-7060

pISSN - 1523-7052

DOI - 10.1021/ol500738g

Subject(s) - chemistry , tetrasaccharide , heparan sulfate , sulfation , disaccharide , sulfate , glycosylation , oligosaccharide , stereochemistry , biochemistry , combinatorial chemistry , organic chemistry , glycosaminoglycan , polysaccharide

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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