Mechanism-based enzyme inactivation using an allyl sulfoxide-allyl sulfenate ester rearrangement

M Johnston, R Raines, C Walsh…

Index: Johnston,M.; Raines,R.; Walsh,C. Journal of the American Chemical Society, 1980 , vol. 102, p. 4241

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Citation Number: 30

Abstract

Abstract: 2-Amino-4-chloro-5-(-nitrophenylsulfinyl) pentanoic acid (1) has been synthesized and shown to induce mechanism-based inactivation of two pyridoxal phosphate dependent enzymes:(1) cystathionine y-synthetase, which catalyzes a y-replacement reaction in bacterial methionine biosynthesis; and (2) methionine y-lyase, which catalyzes a y- elimination reaction in bacterial methionine breakdown. The inactivations are irreversible ...