Stereoselective Synthesis of Boat-Locked Glycosides Designed as Glycosyl Hydrolase Conformational Probes

Autor:	Jérémy Reniers, Emilie Thiery, Johan Wouters, Stéphane P. Vincent
Rok vydání:	2015
Předmět:	chemistry.chemical_classification 010405 organic chemistry Stereochemistry fungi Organic Chemistry Cyclohexane conformation Glycoside Substrate (chemistry) 010402 general chemistry 01 natural sciences 0104 chemical sciences Stereocenter body regions chemistry.chemical_compound chemistry Hydrolase Stereoselectivity Glycosyl Glycoside hydrolase Physical and Theoretical Chemistry
Zdroj:	European Journal of Organic Chemistry. 2015:1472-1484
ISSN:	1434-193X
DOI:	10.1002/ejoc.201403363
Popis:	A general method for the preparation of galactose derivatives locked in a 1,4B boat conformation has been developed. The boat scaffold was stereoselectively functionalized at the C-1′ position by aliphatic and aromatic groups along with azido or hydroxy groups. The configuration at the new stereogenic center was controlled and determined by X-ray diffraction. These molecules were designed to probe the conformational itinerary of the substrate of glycosyl hydrolases. Inhibition assays were performed against a series of commercially available glycosidases, which showed that these enzymes do not harness a 1,4B-boat-like transition state.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::ae773185e877ccb0c5a984297a24ada2 https://doi.org/10.1002/ejoc.201403363 Zobrazit plný text záznamu Plný text ve formátu PDF Plný text ve formátu HTML
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