title: Five-membered ring azasugars as potent inhibitors of alpha-L-rhamnosidase (naringinase) from Penicillium decumbens.
abstract: 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.
authors.affiliation: Department of Chemistry, Scripps Research Institute, La Jolla, CA 92037, USA.
authors.forename: L
authors.initials: L
authors.lastname: Provencher
authors.forename: D H
authors.initials: DH
authors.lastname: Steensma
authors.forename: C H
authors.initials: CH
authors.lastname: Wong
mesh_terms: 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
chemical_list: D001372:Aza Compounds; D009097:Multienzyme Complexes; D006026:Glycoside Hydrolases; C039827:naringinase; D001617:beta-Glucosidase; D012210:Rhamnose