title: Glycosidase inhibition by all 10 stereoisomeric 2,5-dideoxy-2,5-iminohexitols prepared from the enantiomers of glucuronolactone.
abstract: The enantiomers of glucuronolactone are excellent chirons for the synthesis of the 10 stereoisomeric 2,5-dideoxy-2,5-iminohexitols by formation of the pyrrolidine ring by nitrogen substitution at C2 and C5, with either retention or inversion of configuration; the stereochemistry at C3 may be adjusted during the synthesis to give seven stereoisomers from each enantiomer. A definitive side-by-side comparison of the glycosidase inhibition of a panel of 13 glycosidases showed that 8 of the 10 stereoisomers showed significant inhibition of at least one glycosidase.
authors.affiliation: Chemistry Research Laboratory, Department of Chemistry, University of Oxford, Mansfield Road, Oxford OX1 3TA, UK.
authors.forename: Benjamin J
authors.initials: BJ
authors.lastname: Ayers
authors.forename: Nigel
authors.initials: N
authors.lastname: Ngo
authors.forename: Sarah F
authors.initials: SF
authors.lastname: Jenkinson
authors.forename: R Fernando
authors.initials: RF
authors.lastname: Martínez
authors.forename: Yousuke
authors.initials: Y
authors.lastname: Shimada
authors.forename: Isao
authors.initials: I
authors.lastname: Adachi
authors.forename: Alexander C
authors.initials: AC
authors.lastname: Weymouth-Wilson
authors.forename: Atsushi
authors.initials: A
authors.lastname: Kato
authors.forename: George W J
authors.initials: GW
authors.lastname: Fleet
mesh_terms: D004791:Enzyme Inhibitors / Q000138:chemical synthesis* / Q000494:pharmacology*; D005965:Glucuronates / Q000737:chemistry*; D006026:Glycoside Hydrolases / Q000037:antagonists & inhibitors* / Q000737:chemistry*; D050111:Imino Sugars / Q000138:chemical synthesis* / Q000494:pharmacology*; D013237:Stereoisomerism; D013329:Structure-Activity Relationship
chemical_list: D004791:Enzyme Inhibitors; D005965:Glucuronates; D050111:Imino Sugars; C004940:glucuronolactone; D006026:Glycoside Hydrolases