A Versatile Synthetic Strategy for the Preparation and Discovery of New Iminocyclitols as Inhibitors of Glycosidases

Autor:	Maki Takebayashi, Chi-Huey Wong, Sayoko Hiranuma, Osamu Kanie, Yoshimi Kanie, Tetsuya Kajimoto
Rok vydání:	1999
Předmět:	chemistry.chemical_compound Enzyme inhibition Capillary electrophoresis Chemistry Organic Chemistry Side chain Hydroxymethyl Combinatorial chemistry Pyrrolidine
Zdroj:	The Journal of Organic Chemistry. 64:5280-5291
ISSN:	1520-6904 0022-3263
Popis:	A series of iminocyclitols was prepared using a versatile synthetic strategy, and their inhibition of glycosidases was evaluated using capillary electrophoresis. The study has demonstrated that remarkable specificities in enzyme inhibition can be achieved with small modifications on the aglycon side chain and the ring nitrogen. Among the compounds synthesized, (2R,3R,4R,5R)-N-methyl-2-(acetamidomethyl)-3,4-dihydroxy-5-(hydroxymethyl)pyrrolidine was found to be very potent against β-N-acetylhexosaminidase P with the Ki value of 80 nM.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_dedup___::29e03926e37501d56aedd59c73a3a6c8 https://doi.org/10.1021/jo9902446 Zobrazit plný text záznamu