Efficient chemoenzymatic synthesis of novel galacto-N-biose derivatives and their sialylated forms

Lei Li; Yonghui Liu; Tiehai Li; Wenjun Wang; Zaikuan Yu; Cheng Ma; Jingyao Qu; Wei Zhao; Xi Chen; Peng G. Wang

doi:10.1039/C5CC03746H

Efficient chemoenzymatic synthesis of novel galacto-N-biose derivatives and their sialylated forms†

Lei Li,*^ab Yonghui Liu,^b Tiehai Li,^a Wenjun Wang,^b Zaikuan Yu,^a Cheng Ma,^a Jingyao Qu,^a Wei Zhao,^b Xi Chen^c and Peng G. Wang*^a

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* Corresponding authors

^a Department of Chemistry and Center for Diagnostics & Therapeutics, Georgia State University, Atlanta, USA
E-mail: lli22@gsu.edu, pwang11@gsu.edu

^b State Key Laboratory of Medicinal Chemical Biology and College of Pharmacy, Nankai University, Tianjin 300071, P. R. China

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

Abstract

Galacto-N-biose (GNB) derivatives were efficiently synthesized from galactose derivatives via a one-pot two-enzyme system containing two promiscuous enzymes from Bifidobacterium infantis: a galactokinase (BiGalK) and a D-galactosyl-β1–3-N-acetyl-D-hexosamine phosphorylase (BiGalHexNAcP). Mono-sialyl and di-sialyl galacto-N-biose derivatives were then prepared using a one-pot two-enzyme system containing a CMP-sialic acid synthetase and an α2–3-sialyltransferase or an α2–6-sialyltransferase.

Chemical Communications

Efficient chemoenzymatic synthesis of novel galacto-N-biose derivatives and their sialylated forms†

Abstract

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Efficient chemoenzymatic synthesis of novel galacto-N-biose derivatives and their sialylated forms

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