Enzymatic approach to the synthesis of taurine-containing peptides

Subtilisins (subtilopeptidase A, nagarse) and proteinase K were able to catalyze the synthesis of taurine-containing peptides from various N-acylated amino acid or peptide esters and nonprotected taurine. The synthesis was optimized using a model reaction between Boc-Tyr-OMe and taurine. The best results were obtained under strongly alkaline conditions in acetonitrile with low water content as the reaction medium. The choice of the base added to the reaction medium had a substantial effect on the product yield. A preparative synthesis of Tyr-Tau and Ala-Phe-Tau is described.