Enzymatic modular assembly of hybrid Lewis antigens

Hui Xia; Jinfeng Ye; Hongzhi Cao; Xianwei Liu; Yan Zhang; Chang-Cheng Liu

doi:10.1039/D1OB01579F

Enzymatic modular assembly of hybrid Lewis antigens†

Hui Xia,^a Jinfeng Ye,^bc Hongzhi Cao,^abc Xianwei Liu,^a Yan Zhang

*^d and Chang-Cheng Liu

*^ab

Author affiliations

* Corresponding authors

^a National Glycoengineering Research Center, NMPA Key Laboratory for Quality Research and Evaluation of Carbohydrate-Based Medicine, and Shandong Key Laboratory of Carbohydrate Chemistry and Glycobiology, Shandong University, Qingdao 266237, China
E-mail: ccliu@sdu.edu.cn

^b Laboratory for Marine Drugs and Bioproducts, Pilot National Laboratory for Marine Science and Technology (Qingdao), Qingdao 266237, China

^c Key Laboratory of Marine Drugs of Ministry of Education, Shandong Key Laboratory of Glycoscience and Glycotechnology, School of Medicine and Pharmacy, Ocean University of China, Qingdao 266003, China

^d Department of Pharmacy, Qilu Hospital of Shandong University, Jinan 250012, China
E-mail: zhangyansdu@email.sdu.edu.cn

Abstract

The enzymatic synthesis of hybrid Lewis antigens including KH-1 (Lewis y-Lewis x-Lactose, Le^y-Le^x-Lac), Lewis a-Lewis x-Lactose (Le^a-Le^x-Lac), and Lewis b-Lewis x-Lactose (Le^b-Le^x-Lac) has been achieved using a facile enzymatic modular assembly strategy. Starting from a readily available tetrasaccharide, 3 complex hybrid Lewis antigens were achieved in over 40% total yields in less than 5 linear steps of sequential enzymatic glycosylation using 6 enzyme modules. The regio-selective fucosylation was achieved by simply controlling the donor–acceptor ratio. This strategy provides an easy access to these biologically important complex hybrid Lewis antigens at preparative scales.

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

Supplementary files

Article information

DOI: https://doi.org/10.1039/D1OB01579F
Article type: Paper
Submitted: 11 Aug 2021
Accepted: 26 Aug 2021
First published: 26 Aug 2021

Download Citation

Org. Biomol. Chem., 2021,19, 8041-8048

Permissions

Request permissions

Enzymatic modular assembly of hybrid Lewis antigens

H. Xia, J. Ye, H. Cao, X. Liu, Y. Zhang and C. Liu, Org. Biomol. Chem., 2021, 19, 8041 DOI: 10.1039/D1OB01579F

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Organic & Biomolecular Chemistry

Enzymatic modular assembly of hybrid Lewis antigens†

Abstract

Supplementary files

Article information

Download Citation

Permissions

Enzymatic modular assembly of hybrid Lewis antigens

Social activity

Search articles by author

Spotlight

Advertisements