Collect. Czech. Chem. Commun. 1986, 51, 1352-1360

Synthesis of pressinoic acid by enzymatically catalyzed formation of peptide bonds

Václav Čeřovský

Institute of Organic Chemistry and Biochemistry, Czechoslovak Academy of Sciences, 166 10 Prague 6


Three fully enzymatic syntheses of the 1-6 vasopressin hexapeptide were investigated using papain, α-chymotrypsin and thermolysin. Best results were obtained with thermolysin in the 2 + 4 fragment condensation. The α-chymotrypsin-catalyzed 3 + 3 condensation is less advantageous and the 4 + 2 condensation with papain gave only low yield. Using the mentioned enzymes, further fragments of vasopressin molecule were prepared. Amino groups were protected with benzoylcarbonyl or tert-butyloxycarbonyl groups, carboxyl groups as phenylhydrazides or methyl esters, and the cysteine sulfhydryl group as the benzyl derivate. The tyrosine hydroxyl was not protected.