ENZYMATIC APPROACH TO THE SYNTHESIS OF TAURINE-CONTAINING PEPTIDES

Subtilisins (subtilopeptidase A, nagarse) and proteinase K were able t o catalyze the synthesis of taurine-containing peptides from various N -acylated amino acid or peptide esters and nonprotected taurine. The s ynthesis was optimized using a model reaction between Boc-Tyr-OMe and taurine. The best results were obtained under strongly alkaline condit ions in acetonitrile with low water content as the reaction medium. Th e choice of the base added to the reaction medium had a substantial ef fect on the product yield. A preparative synthesis of Tyr-Tau and Ala- Phe-Tau is described. (C) Munksgaard 1994.