A Simple Approach for the Synthesis of Thio-, Dithio- and Selenothio-carbamate-Tethered Peptidomimetics

摘要

A simple and efficient method is described for the syn-thesis of thio-, dithio- and selenothiocarbamate-linked peptidomi-metics. The nucleophilic addition of enantiopure N'-protected amino alkyl thiols to isocyanates, isothiocyanates or isoselenocya-nates obtained from amino acid esters proceeds smoothly in the presence of catalytic amount of DMAP. The protocol was further extended for the synthesis of N,N'-orthogonally protected thio-, di-thio- and selenothiocarbamate-linked peptidomimetics. The reac-tion is mild, free from racemization, and the products were obtained in good yield.