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Efficiently Synthesizing Lacto‐Ganglio‐Series Gangliosides by Using a Glucosyl Ceramide Cassette Approach: The Total Synthesis of Ganglioside X2
Author(s) -
Nakashima Shinya,
Ando Hiromune,
Saito Risa,
Tamai Hideki,
Ishida Hideharu,
Kiso Makoto
Publication year - 2012
Publication title -
chemistry – an asian journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.18
H-Index - 106
eISSN - 1861-471X
pISSN - 1861-4728
DOI - 10.1002/asia.201100928
Subject(s) - ganglioside , ceramide , trisaccharide , tetrasaccharide , glycosylation , chemistry , glycan , total synthesis , stereochemistry , galactose , biochemistry , polysaccharide , glycoprotein , apoptosis
The first total synthesis of the hybrid ganglioside X2, which consisted of a highly branched octasaccharide and ceramide moieties, was accomplished by using a glucosyl ceramide cassette approach. With a disaccharyl donor, the heptasaccharide could not be constructed by glycosylation of the C4 hydroxy group of galactose at the reducing end of the pentasaccharide. In contrast, through an alternative approach with two branched glycan units, a GM2‐core trisaccharide, and a lacto‐ganglio tetrasaccharide, the heptasaccharyl donor could be prepared and subsequently joined with a glucosyl ceramide cassette to afford the protected ganglioside, X2. Finally, global deprotection completed the synthesis, thus affording the pure ganglioside X2.