PROLINE AS NUCLEOPHILE IN KINETICALLY CONTROLLED PEPTIDE-SYNTHESIS CATALYZED BY ALCALASE IN 2-METHYL-2-PROPANOL

Procedures have been developed to synthesize proline-containing peptides in good yields and high purities via a kinetically controled approach using an industrial alkaline protease, alcalase, as a catalyst in anhydrous 2-methyl-2-propanol. The yield of the reaction was dependent on the structure of the acyl-donor and the water content in the solvent. Using tripeptide as an acyl donor, the yield was higher than that using dipeptide, and when amino acid derivatives were used the yield was the lowest. The yield was also dependent on the concentration of water present in the solvent. The higher the water concentration in the solvent, the lower was the yield in the reaction. Both L-proline or D-proline derivatives could be used as nucleophiles in the reaction.