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 journalArticle

16 Citations (Scopus)

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

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Tumor-Associated Carbohydrate Antigens
Antigens
Carbohydrates
Tumors
Gangliosides
Glycosylation
Stereoselectivity
Oligosaccharides
Electronic properties
Fucosyltransferases
Sialyltransferases
Chemical activation
stage-specific embryonic antigen-3
stage-specific embryonic antigen-4
Globo-H

Keywords

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

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

Cite this

Chemoenzymatic syntheses of tumor-associated carbohydrate antigen globo-H and stage-specific embryonic antigen 4. / Wang, Zhen; Gilbert, Michel; Eguchi, Hironobu; Yu, Hai; Cheng, Jiansong; Muthana, Saddam; Zhou, Luyuan; Wang, Peng George; Chen, Xi; Huang, Xuefei.

In: Advanced Synthesis and Catalysis, Vol. 350, No. 11-12, 04.08.2008, p. 1717-1728.

Research output: Contribution to journalArticle

Wang, Z, Gilbert, M, Eguchi, H, Yu, H, Cheng, J, Muthana, S, Zhou, L, Wang, PG, Chen, X & Huang, X 2008, 'Chemoenzymatic syntheses of tumor-associated carbohydrate antigen globo-H and stage-specific embryonic antigen 4', Advanced Synthesis and Catalysis, vol. 350, no. 11-12, pp. 1717-1728. https://doi.org/10.1002/adsc.200800129
Wang, Zhen ; Gilbert, Michel ; Eguchi, Hironobu ; Yu, Hai ; Cheng, Jiansong ; Muthana, Saddam ; Zhou, Luyuan ; Wang, Peng George ; Chen, Xi ; Huang, Xuefei. / Chemoenzymatic syntheses of tumor-associated carbohydrate antigen globo-H and stage-specific embryonic antigen 4. In: Advanced Synthesis and Catalysis. 2008 ; Vol. 350, No. 11-12. pp. 1717-1728.
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