A novel enzymatic method for synthesis of glycopeptides carrying natural eukaryotic N-glycans

Yangyang Xu; Zhigang Wu; Peiru Zhang; He Zhu; Hailiang Zhu; Qitao Song; Li Wang; Faxing Wang; Peng George Wang; Jiansong Cheng

doi:10.1039/C7CC04362G

A novel enzymatic method for synthesis of glycopeptides carrying natural eukaryotic N-glycans†

Yangyang Xu,‡^a Zhigang Wu,‡^b Peiru Zhang,^a He Zhu,^b Hailiang Zhu,^b Qitao Song,^a Li Wang,^a Faxing Wang,^a Peng George Wang*^a and Jiansong Cheng

*^a

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* Corresponding authors

^a State Key Laboratory of Medicinal Chemical Biology and College of Pharmacy, Nankai University, Haihe Education Park, 38 Tongyan Road, Tianjin 300353, P. R. China
E-mail: pwang@nankai.edu.cn, jiansongcheng@nankai.edu.cn

^b Department of Chemistry, Georgia State University, Atlanta, Georgia 30303, USA

Abstract

A novel enzymatic approach was developed for facile production of glycopeptides carrying natural eukaryotic N-glycans. In this approach, peptides can be GlcNAcylated at one or two natural N-glycosylation sites via two-step enzymatic reactions catalyzed by an evolved N-glycosyltransferase (ApNGT^Q469A) and a glucosamine N-acetyltransferase (GlmA), respectively. The resulting GlcNAc-peptides were further modified by an endo-β-N-acetylglucosaminidase M mutant (EndoM^N175Q) to generate glycopeptides. In three steps of enzymatic catalysis, glycopeptides carrying complex-type N-glycans can be efficiently synthesized.

Chemical Communications

A novel enzymatic method for synthesis of glycopeptides carrying natural eukaryotic N-glycans†

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A novel enzymatic method for synthesis of glycopeptides carrying natural eukaryotic N-glycans

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