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Total Synthesis of Sulfated Glycosphingolipid SM1a, a Kind of Human Epithelial Carcinoma Antigen
Author(s) -
Zhang Pengtao,
Wang Kun,
Zhang Jun,
Li Chunxia,
Guan Huashi
Publication year - 2015
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201403296
Subject(s) - glycosphingolipid , chemistry , trisaccharide , ganglioside , sulfation , ceramide , stereochemistry , residue (chemistry) , galactose , glycosylation , glycolipid , biochemistry , antigen , immunology , biology , apoptosis
A highly efficient and practical total synthesis of the sulfated ganglioside SM1a, a kind of human epithelial carcinoma antigen identified in mammalian kidney, has been accomplished for the first time. The characteristic sequence of SM1a, β‐ D ‐Gal p ‐(1→3)‐β‐ D ‐NHAcGal p ‐(1→4)‐β‐ D ‐(3‐ O ‐sulfate)‐Gal p ‐(1→4)‐β‐ D ‐Glc p ‐ceramide was assembled by a [3+2] convergent approach. A key trisaccharide building block was formed from a new galactose acceptor 7 containing a potential sulfated site, GalNHTroc donor 6 , and galactose donor 4 . The cyclic glucosyl ceramide was glycosylated with trisaccharide trichloroacetimidate 2 to give the protected ganglioside backbone in good yield. Selective sulfonation at the 3‐OH of the Gal residue followed by global deprotection gave the target molecule SM1a.