Five-membered ring azasugars as potent inhibitors of alpha-L-rhamnosidase (naringinase) from Penicillium decumbens.
Five-membered ring azasugars with the L-rhamnose configuration were synthesized as inhibitors of alpha-L-rhamnosidase from Penicillium decumbens. All compounds tested were in the microM or sub-microM range. Substitution at the nitrogen shifted the inhibition mechanism from mixed to competitive.
Provencher
L
L
Department of Chemistry, Scripps Research Institute, La Jolla, CA 92037, USA.
Steensma
D H
DH
Wong
C H
CH
D001372:Aza Compounds / Q000138:chemical synthesis* / Q000494:pharmacology*; D006026:Glycoside Hydrolases / Q000037:antagonists & inhibitors* / Q000378:metabolism; D007700:Kinetics; D009097:Multienzyme Complexes / Q000037:antagonists & inhibitors* / Q000378:metabolism; D010407:Penicillium / Q000201:enzymology; D012210:Rhamnose / Q000737:chemistry; D001617:beta-Glucosidase / Q000037:antagonists & inhibitors* / Q000378:metabolism
D001372:Aza Compounds; D009097:Multienzyme Complexes; D006026:Glycoside Hydrolases; C039827:naringinase; D001617:beta-Glucosidase; D012210:Rhamnose