Identification of the binding roles of terminal and internal glycan epitopes using enzymatically synthesized: N -glycans containing tandem epitopes

Zhigang Wu, Yunpeng Liu, Cheng Ma, Lei Li, Jing Bai, Lauren Byrd-Leotis, Yi Lasanajak, Yuxi Guo, Liuqing Wen, He Zhu, Jing Song, Yanhong Li, David A. Steinhauer, David F. Smith, Baohua Zhao, Xi Chen, Wanyi Guan, Peng George Wang

Research output: Contribution to journalArticlepeer-review

21 Scopus citations


Glycans play diverse roles in a wide range of biological processes. Research on glycan-binding events is essential for learning their biological and pathological functions. However, the functions of terminal and internal glycan epitopes exhibited during binding with glycan-binding proteins (GBPs) and/or viruses need to be further identified. Therefore, a focused library of 36 biantennary asparagine (Asn)-linked glycans with some presenting tandem glycan epitopes was synthesized via a combined Core Isolation/Enzymatic Extension (CIEE) and one-pot multienzyme (OPME) synthetic strategy. These N-glycans include those containing a terminal sialyl N-acetyllactosamine (LacNAc), sialyl Lewis x (sLex) and Siaα2-8-Siaα2-3/6-R structures with N-acetylneuraminic acid (Neu5Ac) or N-glycolylneuraminic acid (Neu5Gc) sialic acid form, LacNAc, Lewis x (Lex), α-Gal, and Galα1-3-Lex; and tandem epitopes including α-Gal, Lex, Galα1-3-Lex, LacNAc, and sialyl LacNAc, presented with an internal sialyl LacNAc or 1-2 repeats of an internal LacNAc or Lex component. They were synthesized in milligram-scale, purified to over 98% purity, and used to prepare a glycan microarray. Binding studies using selected plant lectins, antibodies, and viruses demonstrated, for the first time, that when interpreting the binding between glycans and GBPs/viruses, not only the structure of the terminal glycan epitopes, but also the internal epitopes and/or modifications of terminal epitopes needs to be taken into account.

Original languageEnglish (US)
Pages (from-to)11106-11116
Number of pages11
JournalOrganic and Biomolecular Chemistry
Issue number47
StatePublished - 2016

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry


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