Synthesis and enzymatic susceptibility of a series of novel GM2 analogs |
| |
| Authors: | Tomoaki Fuse Hiromune Ando Akihiro Imamura Naoki Sawada Hideharu Ishida Makoto Kiso Takayuki Ando Su-Chen Li Yu-Teh Li |
| |
| Institution: | (1) Department of Applied Bio-organic Chemistry, Gifu University, Gifu 501-1193, Japan;(2) Division of Instrumental analysis, Life Science Research Center, Gifu University, Gifu 501-1193, Japan;(3) Department of Applied Bio-organic Chemistry, Gifu University, Gifu 501-1193, Japan;(4) CREST, Japan Science and Technology Agency (JST), Tokyo, Japan;(5) Department of Biochemistry, Tulane University Health Science Center School of Medicine, 1430 Tulane Avenue, New Orleans, 70112, Louisiana;(6) Present address: Center for Emerging Infectious Diseases, Gifu University, Gifu 501-1193, Japan |
| |
| Abstract: | A series of GM2 analogs in which GM2 epitope was coupled to a variety of glycosyl lipids were designed and synthesized to
investigate the mechanism of enzymatic hydrolysis of GM2 ganglioside. The coupling of N-Troc-protected sialic acid and p-methoxyphenyl galactoside acceptor gave the crystalline disaccharide, which was further coupled with galactosamine donor
to give the desired GM2 epitope trisaccharide. After conversion into the corresponding glycosyl donor, the trisaccharide was
coupled with galactose, glucose and artificial ceramide (B30) to give the final compounds. The result on hydrolysis of GM2
analogs indicates that GM2 activator protein requires one spacer sugar between GM2 epitope and the lipid moiety to assist
the hydrolysis of the terminal GalNAc residue.
Synthetic studies on sialoglycoconjugates, Part 140. For part 139, see Ref 1]. |
| |
| Keywords: | GM2 ganglioside GM2 epitope GM2 activator Artificial ceramide |
| 本文献已被 PubMed SpringerLink 等数据库收录！ |
|
