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Li L, Liu Y, Ma C, et al. Efficient Chemoenzymatic Synthesis of an N-glycan Isomer Library. Chem Sci. 2015;6(10):5652-5661doi: 10.1039/C5SC02025E.
Li, L., Liu, Y., Ma, C., Qu, J., Calderon, A. D., Wu, B., Wei, N., Wang, X., Guo, Y., Xiao, Z., Song, J., Sugiarto, G., Li, Y., Yu, H., Chen, X., & Wang, P. G. (2015). Efficient Chemoenzymatic Synthesis of an N-glycan Isomer Library. Chemical science, 6(10), 5652-5661. https://doi.org/10.1039/C5SC02025E
Li, Lei, et al. "Efficient Chemoenzymatic Synthesis of an N-glycan Isomer Library." Chemical science vol. 6,10 (2015): 5652-5661. doi: https://doi.org/10.1039/C5SC02025E
Li L, Liu Y, Ma C, Qu J, Calderon AD, Wu B, Wei N, Wang X, Guo Y, Xiao Z, Song J, Sugiarto G, Li Y, Yu H, Chen X, Wang PG. Efficient Chemoenzymatic Synthesis of an N-glycan Isomer Library. Chem Sci. 2015 Oct 01;6(10):5652-5661. doi: 10.1039/C5SC02025E. Epub 2015 Jun 23. PMID: 26417422; PMCID: PMC4583208.
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Chem Sci. 2015 Oct 01;6(10):5652-5661. doi: 10.1039/C5SC02025E. Epub 2015 Jun 23.

Efficient Chemoenzymatic Synthesis of an N-glycan Isomer Library.

Chemical science

Lei Li, Yunpeng Liu, Cheng Ma, Jingyao Qu, Angie D Calderon, Baolin Wu, Na Wei, Xuan Wang, Yuxi Guo, Zhongying Xiao, Jing Song, Go Sugiarto, Yanhong Li, Hai Yu, Xi Chen, Peng George Wang

Affiliations

  1. Department of Chemistry and Center of Diagnostics & Therapeutics, Georgia State University, 50 Decatur St SE, Atlanta, GA 30303.
  2. Chemily, LLC, 58 Edgewood Ave NE, Atlanta, GA 30303.
  3. Department of Chemistry, University of California, Davis, One Shields Avenue, Davis, CA 95616.

PMID: 26417422 PMCID: PMC4583208 DOI: 10.1039/C5SC02025E

Abstract

Quantification, characterization and biofunctional studies of N-glycans on proteins remain challenging tasks due to complexity, diversity and low abundance of these glycans. The availability of structurally defined N-glycans (especially isomers) libraries is essential to help on solving these tasks. We reported 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 the 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 enzymatic extension. 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 MS

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