Organophosphorus Analogues and Derivatives of the Natural l-Amino Carboxylic Acids and Peptides. II. Synthesis, Enzyme-Substrate Interactions of “Bialaphos” (SF-1293) and Its Cyclic and Phosphinic Amide Type Analogues

The natural tripeptide antibiotic “Bialaphos” (5) has been synthesized by condensation of the protected l-phosphinothricin (1) with the dipeptide alanylalanine ethyl ester. The dicyclohexylcarbodiimide method has been used, followed by enzyme-catalyzed hydrolysis. Analogously, a cyclic analogue and the phosphac-peptide (phosphinic amide type) analogue (14) of the antibiotic (5) have been found to possess antitumour activity.