Facile chemoenzymatic synthesis of biotinylated heparosan hexasaccharide

Baolin Wu; Na Wei; Vireak Thon; Mohui Wei; Zaikuan Yu; Yongmei Xu; Xi Chen; Jian Liu; Peng George Wang; Tiehai Li

doi:10.1039/C5OB00462D

Facile chemoenzymatic synthesis of biotinylated heparosan hexasaccharide†

Baolin Wu,‡^a Na Wei,‡^a Vireak Thon,^a Mohui Wei,^a Zaikuan Yu,^a Yongmei Xu,^b Xi Chen,^c Jian Liu,^b Peng George Wang*^a and Tiehai Li*^a

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* Corresponding authors

^a Center for Diagnostics and Therapeutics, Department of Chemistry, Georgia State University, Atlanta, GA 30303, USA
E-mail: tli8@gsu.edu, pwang11@gsu.edu

^b Division of Chemical Biology and Medicinal Chemistry, Eshelman School of Pharmacy, University of North Carolina, Chapel Hill, NC 27599, USA

^c Department of Chemistry, University of California, One Shields Avenue, Davis, CA 95616, USA

Abstract

A biotinylated heparosan hexasaccharide was synthesized using a one-pot multi-enzyme strategy, in situ activation and transfer of N-trifluoroacetylglucosamine (GlcNTFA) to a heparin backbone significantly improved the synthetic efficiency. The biotinylated hexasaccharide could serve as a flexible core to diversify its conversion into heparan sulfate isoforms with potential biological applications and therapeutics.

Organic & Biomolecular Chemistry

Facile chemoenzymatic synthesis of biotinylated heparosan hexasaccharide†

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Facile chemoenzymatic synthesis of biotinylated heparosan hexasaccharide

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