Chemoenzymatic syntheses of tumor-associated carbohydrate antigen globo-H and stage-specific embryonic antigen 4

Zhen Wang, Michel Gilbert, Hironobu Eguchi, Hai Yu, Jiansong Cheng, Saddam Muthana, Luyuan Zhou, Peng George Wang, Xi Chen, Xuefei Huang

Research output: Contribution to journalArticlepeer-review

18 Scopus citations

Abstract

Gangliosides have attracted much attention due to their important biological properties. Herein we report the first chemoenzymatic syntheses oftwo globo series of ganglioside oligosaccharides, Globo-H 1 and stage-specific embryonic antigen-4 (SSEA-4) 2. The common precursor SSEA-3 pentasaccharide for these two compounds was assembled rapidly using the pre-activation-based one-pot glycosylation method. The stereoselectivity in forming the 1,2-cis linkage in SSEA-3 was attributed to a steric buttressing effect of the donor rather than electronic properties ofthe glycosyl donors. SSEA-3 was then successfully fucosylated by the fucosyltransferase WbsJ and sialylated by sialyltransferases CST-I and PmST1 producing Globo-H and SSEA-4, respectively.

Original languageEnglish (US)
Pages (from-to)1717-1728
Number of pages12
JournalAdvanced Synthesis and Catalysis
Volume350
Issue number11-12
DOIs
StatePublished - Aug 4 2008

Keywords

  • Carbohydrates
  • Chemoenzymatic synthesis
  • Natural products
  • Oligosaccharides
  • Stereoselectivity

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

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