MODELS THAT DEMONSTRATE PEPTIDE BOND FORMATION BY PRIOR THIOL CAPTURE I. CAPTURE BY DISULFIDE FORMATION

Article abstract of DOI:10.1016/0040-4039(81)80049-4

Unsymmetrical disulfides formed from L-cysteine esters and o-Cbz-L-alaninyloxybenzenethiol 9, 2-Cbz-L-alaninyloxy-5-chlorophenylmethylenethiol 8, 4-acetoxyxanthenylmethylenethiol 10, and 1,5-diacetoxy-2-methyl-3-methoxy-4-thioxanthone 11 are observed to undergo intramolecular O,N-acyl transfer in yields up to 60percent, with accompanying disulfide interchange.The significance of these results for a general amide forming strategy of prior cysteine capture are discussed.