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Fluorous-assisted chemoenzymatic synthesis of heparan sulfate oligosaccharides.

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.

SUBMITTER: Cai C

PROVIDER: S-EPMC3998769 | biostudies-literature | 2014 Apr

REPOSITORIES: biostudies-literature

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Fluorous-assisted chemoenzymatic synthesis of heparan sulfate oligosaccharides.

Cai Chao C Dickinson Demetria M DM Li Lingyun L Masuko Sayaka S Suflita Matt M Schultz Victor V Nelson Shawn D SD Bhaskar Ujjwal U Liu Jian J Linhardt Robert J RJ

Organic letters 20140404 8

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 oligo ...[more]

PMID: 24697306

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