Models that demonstrate peptide bond formation by prior thiol capture I. Capture by disulfide formation

DS Kemp, SL Leung, DJ Kerkman

Index: Kemp, D. S.; Leung, See-Lap; Kerkman, Daniel J. Tetrahedron Letters, 1981 , vol. 22, p. 181 - 184

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Citation Number: 31

Abstract

Abstract: Unsymmetrical disulfides formed from C-cysteine esters and c-Cbz-C- alaninyloxybenzenethiol 2, P-Cbz-C-alaninyloxy-5-chlorophenylmethylenethiol@, 4_acetoxyxanthenylmethylene thiol j $, and 1, 5-diacetoxy-2-methy1-3-methoxy-4- thioxanthone ii are observed to undergo intramolecular O, N-acyl transfer in yields up to 60%, with accompanying disulfide interchange. The significance of these results for a ...