An approach to the prevention of racemisation in the synthesis of histidine-containing peptides

Abstract

N(α)-Benzyloxycarbonyl-N(τ)-phenacyl-L-histidine and N(α)-benzyloxycarbonyl-N(π)-phenacyl-L-histidine have been prepared; extensive racemisation of the histidine residue occurs on activation of the former by means of dicyclohexylcarbodi-imide, but not with the N(π)-phenacyl acid.