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Issue 10, 2015
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Efficient chemoenzymatic synthesis of an N-glycan isomer library

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Abstract

Quantification, characterization and biofunctional studies of N-glycans on proteins remain challenging tasks due to the complexity, diversity and low abundance of these glycans. The availability of structurally defined N-glycan (especially isomer) libraries is essential to help solve these tasks. We report herein an efficient chemoenzymatic strategy, namely Core Synthesis/Enzymatic Extension (CSEE), for rapid production of diverse N-glycans. Starting with 5 chemically prepared building blocks, 8 N-glycan core structures containing one or two terminal N-acetyl-D-glucosamine (GlcNAc) residue(s) were chemically synthesized via consistent use of oligosaccharyl thioethers as glycosylation donors in a convergent fragment coupling strategy. Each of these core structures was then extended to 5 to 15 N-glycan sequences by enzymatic reactions catalyzed by 4 robust glycosyltransferases. Success in synthesizing N-glycans with Neu5Gc and core-fucosylation further expanded the ability of the enzymatic extension. Meanwhile, high performance liquid chromatography with an amide column enabled rapid and efficient purification (>98% purity) of N-glycans in milligram scales. A total of 73 N-glycans (63 isomers) were successfully prepared and characterized by MS2 and NMR. In summary, the CSEE strategy provides a practical approach for “mass production” of structurally defined N-glycans, which are important standards and probes for glycoscience.

Graphical abstract: Efficient chemoenzymatic synthesis of an N-glycan isomer library

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Supplementary files

Article information


Submitted
05 Jun 2015
Accepted
22 Jun 2015
First published
23 Jun 2015

This article is Open Access
All publication charges for this article have been paid for by the Royal Society of Chemistry

Chem. Sci., 2015,6, 5652-5661
Article type
Edge Article
Author version available

Efficient chemoenzymatic synthesis of an N-glycan isomer library

L. Li, Y. Liu, C. Ma, J. Qu, A. D. Calderon, B. Wu, N. Wei, X. Wang, Y. Guo, Z. Xiao, J. Song, G. Sugiarto, Y. Li, H. Yu, X. Chen and P. G. Wang, Chem. Sci., 2015, 6, 5652
DOI: 10.1039/C5SC02025E

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