Mechanism-based inhibition and stereochemistry of glucosinolate hydrolysis by myrosinase

Biochemistry
S CottazH Driguez

Abstract

Myrosinase is a particular glucosidase which hydrolyzes a variety of plant 1-thio-beta-D-glucosides known as the glucosinolates. This enzyme, which is the only glycosidase able to hydrolyze these naturally occurring thioglucosides, has been found previously to display strong sequence similarities with family 1 O-glycosidases. Myrosinase therefore offers the opportunity to compare the mechanism of enzymatic cleavage of S- vs O-glycosidic bonds. The stereochemistry of hydrolysis of sinigrin by Sinapis alba myrosinase was followed by 1H NMR and the enzyme was found to operate with a mechanism retaining the anomeric configuration at the cleavage point exactly like the related O-glycosidases found in family 1. Myrosinase was readily inactivated by 2-deoxy-2-fluoroglucotropaeolin with inactivation kinetic parameters of Ki = 0.9 mM and ki = 0.083 min-1. Reactivation kinetic parameters were determined in buffer only, with k(react) = 0.015 h-1 and t1/2 = 46 h, and also in the presence of acceptors of transglycosylation. No significant changes were observed in the presence of methyl beta-D-glucoside, but with azide anion the half-life of reactivation was found to be reduced to t1/2 = 20 h. These results suggest that myrosinase inhibition...Continue Reading

References

Jan 1, 1988·Food and Chemical Toxicology : an International Journal Published for the British Industrial Biological Research Association·R McDanellG R Fenwick

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Citations

May 13, 2005·Organic & Biomolecular Chemistry·Aurélie BourderiouxPatrick Rollin
May 24, 2008·Glycobiology·Brian P Rempel, Stephen G Withers
Jun 29, 2000·Annual Review of Biochemistry·H D Ly, S G Withers
Sep 1, 2000·Carbohydrate Research·S J Williams, S G Withers
Mar 11, 1998·Natural Product Reports·P M Dewick
May 23, 2012·Natural Product Reports·Geoffrey E Ravilious, Joseph M Jez
Mar 11, 2008·Chembiochem : a European Journal of Chemical Biology·Jared R MaysScott R Rajski
Jun 7, 2016·Organic & Biomolecular Chemistry·Sami MarrounRichard Daniellou
Oct 8, 2020·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·V P Thinh NguyenFlorent Allais

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