In:
Advanced Synthesis & Catalysis, Wiley, Vol. 350, No. 11-12 ( 2008-08-04), p. 1717-1728
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.
Type of Medium:
Online Resource
ISSN:
1615-4150
,
1615-4169
DOI:
10.1002/adsc.v350:11/12
DOI:
10.1002/adsc.200800129
Language:
English
Publisher:
Wiley
Publication Date:
2008
detail.hit.zdb_id:
2041384-1
detail.hit.zdb_id:
2033084-4
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