Glycoconjugate synthesis using chemoselective ligation

Shuihong Cheng; Paeton L. Wantuch; Megan E. Kizer; Dustin R. Middleton; Ruitong Wang; Mikaela DiBello; Mingli Li; Xing Wang; Xuebing Li; Vasanthi Ramachandiran; Fikri Y. Avci; Fuming Zhang; Xing Zhang; Robert J. Linhardt

doi:10.1039/C9OB00270G

Glycoconjugate synthesis using chemoselective ligation†

Shuihong Cheng,^a Paeton L. Wantuch,^b Megan E. Kizer,

^c Dustin R. Middleton,^b Ruitong Wang,^c Mikaela DiBello,^c Mingli Li,^a Xing Wang,

^c Xuebing Li,

^a Vasanthi Ramachandiran,^d Fikri Y. Avci,^b Fuming Zhang,^c Xing Zhang*^c and Robert J. Linhardt

*^c

Author affiliations

* Corresponding authors

^a CAS Key Laboratory of Pathogenic Microbiology and Immunology, Institute of Microbiology, Chinese Academy of Sciences, Beijing 100101, Chaoyang, China

^b Department of Biochemistry and Molecular Biology, Center for Molecular Medicine, and Complex Carbohydrate Research Center, University of Georgia, Athens, GA 30602, USA

^c Department of Chemistry and Chemical Biology, Center for Biotechnology and Interdisciplinary Studies, Rensselaer Polytechnic Institute, Troy, New York 12180, USA
E-mail: xingzhang-cas@hotmail.com, linhar@rpi.edu

^d NIH Tetramer Core Facility, Emory University, Atlanta, GA 30322, USA

Abstract

Chemoselective ligation of carbohydrates and polypeptides was achieved using an adipic acid dihydrazide cross-linker. The reducing end of a carbohydrate is efficiently attached to peptides in two steps, constructing a glycoconjugate in high yield and with high regioselectivity, enabling the production of homogeneous glycoconjugates.

This article is part of the themed collection: Chemical Biology in OBC

Organic & Biomolecular Chemistry

Glycoconjugate synthesis using chemoselective ligation†

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