1143373-99-2Relevant academic research and scientific papers
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
supporting information; experimental part, p. 1717 - 1728 (2009/11/30)
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.
