The Journal of Organic Chemistry

Racemization mechanism of cysteine dipeptide active ester derivatives

J Kovacs, Y Hsieh

Index: Kovacs, J.; Hsieh, Y. Journal of Organic Chemistry, 1982 , vol. 47, # 25 p. 4996 - 5002

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Citation Number: 5

Abstract

Discussion A distinction between the 5 (4H)-oxazolone and the enolization mechanism of racemization of C-activated peptide derivatives is the following: in the 5 (4H)-oxazolone formation the rate-determining step does not involve the breaking of an a-carbon-hydrogen bond, while in the enolization mechanism the slow step is the removal of cy-hydrogen.+" An earlier report12 demonstrated that the deuterium isotope effect can be used to distinguish ...