title: Donor-bound glycosylation for various glycosyl acceptors: bidirectional solid-phase semisynthesis of vancomycin and its derivatives.
abstract: The glycosidation of a polymer-supported glycosyl donor, N-phenyltrifluoroacetimidate, with various glycosyl acceptors is reported. The application of the polymer-supported N-phenyltrifluoroacetimidate is demonstrated in the synthesis of vancomycin derivatives. 2-O-[2-(azidomethyl)benzoyl]glycosyl imidate was attached to a polymer support at the 6-position by a phenylsulfonate linked with a C13 alkyl spacer. Solid-phase glycosidation with a vancomycin aglycon, selective deprotection of the 2-(azidomethyl)benzoyl group, and glycosylation of the resulting 2-hydroxy group with a vancosamine unit were performed. Nucleophilic cleavage from the polymer support with acetate, chloride, azido, and thioacetate ions provided vancomycin derivatives in pure form after simple purification. The semisynthesis of vancomycin was achieved by deprotection of the acetate derivative.
authors: Department of Applied Chemistry, Tokyo Institute of Technology, 2-12-1 Ookayama, Meguro, Tokyo 152-8552, Japan. doit@apc.titech.ac.jp
authors: Takayuki
authors: T
authors: Doi
authors: Atsushi
authors: A
authors: Kinbara
authors: Hitoshi
authors: H
authors: Inoue
authors: Takashi
authors: T
authors: Takahashi
mesh_terms: D000900:Anti-Bacterial Agents / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D020650:Combinatorial Chemistry Techniques; D015195:Drug Design; D006031:Glycosylation; D015394:Molecular Structure; D011108:Polymers / Q000737:chemistry; D014640:Vancomycin / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D000900:Anti-Bacterial Agents; D011108:Polymers; D014640:Vancomycin