Chemoenzymatic Syntheses of Tumor-Associated Carbohydrate Antigen Globo-H and Stage-Specific Embryonic Antigen 4

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

• Publisher: John Wiley and Sons
• Year: 2008
• Tongue: English
• Weight: 345 KB
• Volume: 350
• Category: Article
• ISSN: 1615-4150
• DOI: 10.1002/adsc.200800129

✦ Synopsis

Abstract

Gangliosides have attracted much attention due to their important biological properties. Herein we report the first chemoenzymatic syntheses of two 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 of the 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.