Syntheses of <i>N</i>-Acyl Dipeptide Derivatives by Metalloproteinases

Abstract

Abstract X–Dipeptides (X=Z, Z(OMe), or Z(3Me)) have been catalytically synthesized by several microbial metalloproteinases. Among the enzymes used, Thermolysin showed the most remarkable ability in the coupling reactions of the esters or the amides of phenylalanine, leucine, isoleucine, and valine (and methionine in the case of the amide) with various X–amino acids. This method has been applied to the syntheses of ZPhePheOMe and ZPhePeOMe on a practical scale. Ammonium sulfate and sodium chloride had a marked effect on the condensed products, increasing the yield.