CHEMICAL STUDIES ON TUBERACTINOMYCIN. XV

TOTAL SYNTHESIS OF TUBERACTINOMYCIN O

Abstract

Tuberactinomycin O, one of the four congeners of the antituberculous peptide tuberactinomycin, was totally synthesized. The β-ureidodehydroalanine moiety was constructed from β, β-diethoxyalanine with excess urea in acidic medium after a cyclization reaction of a pentapeptide was finished. Cyclization was carried out by means of the 1-succinimidyl ester method. To the cyclic pentapeptide, β-lysine was introduced as the branched moiety and then deprotected to afford tuberactinomycin O which was completely identified with the natural form of the antibiotic.