title: Synthesis and enzymatic susceptibility of a series of novel GM2 analogs.
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.
authors.affiliation: Department of Applied Bio-organic Chemistry, Gifu University, Gifu 501-1193, Japan.
authors.forename: Tomoaki
authors.initials: T
authors.lastname: Fuse
authors.forename: Hiromune
authors.initials: H
authors.lastname: Ando
authors.forename: Akihiro
authors.initials: A
authors.lastname: Imamura
authors.forename: Naoki
authors.initials: N
authors.lastname: Sawada
authors.forename: Hideharu
authors.initials: H
authors.lastname: Ishida
authors.forename: Makoto
authors.initials: M
authors.lastname: Kiso
authors.forename: Takayuki
authors.initials: T
authors.lastname: Ando
authors.forename: Su-Chen
authors.initials: SC
authors.lastname: Li
authors.forename: Yu-Teh
authors.initials: YT
authors.lastname: Li
mesh_terms: D004798:Enzymes / Q000737:chemistry / Q000378:metabolism / Q000502:physiology*; D000939:Epitopes / Q000737:chemistry / Q000378:metabolism; D005678:G(M2) Ganglioside / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000737:chemistry / Q000378:metabolism; D006801:Humans; D006868:Hydrolysis; D013661:Tay-Sachs Disease / Q000201:enzymology / Q000378:metabolism
chemical_list: D004798:Enzymes; D000939:Epitopes; D005678:G(M2) Ganglioside