Abstract: Thiol-functionalized surfactant micelles (n-C12H25NfMe2CH2CH2SH, CI-) were used to cleave Z-TrpPro p-nitrophenyl dipeptide esters. Marked kinetic diastereoselectivity was observed in these reactions. For example at pH 8 and concentrations (-6-7) XM, the micellar thiol cleaved the LL substrate 5-6 times more rapidly than its DL diastereomer. This kinetic diastereoselectivity was shown to develop at surfactant concentrations-5 XM), Le., ...
