Conduritol aziridine: a new mechanism-based glucosidase inactivator.
A new mechanism-based glucosidase inactivator, conduritol aziridine (1,2-dideoxy-1,2-epimino-myo-inositol), has been synthesised from myo-inositol. This aziridine inactivates both the beta-glucosidase from Alcaligenes faecalis and the alpha-glucosidase from yeast according to the expected pseudo-first order kinetics. Inactivation constants measured are Ki = 3.0mM, ki = 0.077 min-1 for the beta-glucosidase, and Ki = 9.5mM, ki = 0.39 min-1 for the alpha-glucosidase. Evidence for irreversible inactivation is provided by the lack of reactivation upon dilution of inactivated enzyme into buffer containing substrate.
Caron
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Department of Chemistry, University of British Columbia, Vancouver, Canada.
Withers
S G
SG
D000421:Alcaligenes / Q000201:enzymology; D001388:Aziridines / Q000138:chemical synthesis / Q000494:pharmacology*; D001389:Azirines / Q000494:pharmacology*; D005959:Glucosidases / Q000037:antagonists & inhibitors*; D050112:Imino Pyranoses; D007294:Inositol / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000494:pharmacology; D012441:Saccharomyces cerevisiae / Q000201:enzymology; D013329:Structure-Activity Relationship
D001388:Aziridines; D001389:Azirines; D050112:Imino Pyranoses; C060863:conduritol aziridine; D007294:Inositol; D005959:Glucosidases