title: Looking glass inhibitors: L-DMDP, a more potent and specific inhibitor of alpha-glucosidases than the enantiomeric natural product DMDP.
abstract: L-DMDP, prepared from D-gulonolactone, is a highly specific inhibitor of a number of plant and mammalian alpha-glucosidases [between 2 and 4 orders of magnitude more potent than the enantiomeric natural product DMDP] but is not an inhibitor of bacterial and yeast alpha-glucosidases. Additionally N-butyl-DMDP is a potent inhibitor of ceramide-specific glucosyltransferase but N-butyl-L-DMDP shows no inhibition.
authors.affiliation: Chemistry Research Laboratory, Department of Chemistry, University of Oxford, Mansfield Road, Oxford, UK OX1 3TA.
authors.forename: Chu-Yi
authors.initials: CY
authors.lastname: Yu
authors.forename: Naoki
authors.initials: N
authors.lastname: Asano
authors.forename: Kyoko
authors.initials: K
authors.lastname: Ikeda
authors.forename: Mei-Xiang
authors.initials: MX
authors.lastname: Wang
authors.forename: Terry D
authors.initials: TD
authors.lastname: Butters
authors.forename: Mark R
authors.initials: MR
authors.lastname: Wormald
authors.forename: Raymond A
authors.initials: RA
authors.lastname: Dwek
authors.forename: Ana L
authors.initials: AL
authors.lastname: Winters
authors.forename: Robert J
authors.initials: RJ
authors.lastname: Nash
authors.forename: George W J
authors.initials: GW
authors.lastname: Fleet
mesh_terms: D000470:Alkaloids / Q000138:chemical synthesis* / Q000494:pharmacology; D004791:Enzyme Inhibitors / Q000138:chemical synthesis* / Q000494:pharmacology; D005964:Glucosyltransferases / Q000037:antagonists & inhibitors; D065089:Glycoside Hydrolase Inhibitors; D050113:Imino Furanoses; D008353:Mannitol / Q000031:analogs & derivatives; D015394:Molecular Structure; D011759:Pyrrolidines / Q000138:chemical synthesis* / Q000494:pharmacology; D013237:Stereoisomerism; D013400:Sugar Acids / Q000737:chemistry
chemical_list: D000470:Alkaloids; D004791:Enzyme Inhibitors; D065089:Glycoside Hydrolase Inhibitors; D050113:Imino Furanoses; D011759:Pyrrolidines; D013400:Sugar Acids; C007895:gulonolactone; D008353:Mannitol; C043121:2,5-dihydroxymethyl-3,4-dihydroxypyrrolidine; D005964:Glucosyltransferases