Looking glass inhibitors: L-DMDP, a more potent and specific inhibitor of alpha-glucosidases than the enantiomeric natural product DMDP.
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.
Yu
Chu-Yi
CY
Chemistry Research Laboratory, Department of Chemistry, University of Oxford, Mansfield Road, Oxford, UK OX1 3TA.
Asano
Naoki
N
Ikeda
Kyoko
K
Wang
Mei-Xiang
MX
Butters
Terry D
TD
Wormald
Mark R
MR
Dwek
Raymond A
RA
Winters
Ana L
AL
Nash
Robert J
RJ
Fleet
George W J
GW
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
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