Phosphonodipeptides

Abstract

Peptides of aminoalkanephosphonic acids (Phosphonopeptides) 4, are now receiving considerable interest because some representatives of this class were found to repress bacterial growth at very low concentration levels 1-3. Literature data on the synthesis of dipeptides containing aminoalkylphosphonic acids are scarce and very little information is avaiable on blocking and deblocking of the phosphonate moiety 3-9. In this communication we report synthesis of dipeptides containing P-terminal aminoalkylphosphonic acids related structurally to glycine,alanine,nor-valine,valine,leucine,phenylglycine and phenylalanine,while the N-terminal residues include glycine,alanine,valine,leucine,proline,methionine,beta-alanine,phenylalanine,tyrosine,lysine and glutamine. The peptides 3 were prepared by condensation of phtaloyl,N-carbobenzoxy,N-t-butoxycarbonyl or N-formylamino acids with 1-aminoalkanephosphonic acids as well as with their dialkyl or diphenyl esters /Scheme/. Special attention was payed on the efectiveness of the peptide bond formation and on the methods for selective and total removal of the blocking groups. The literature data on the preparation of phosphonodipeptides from 1-aminoalkanephosphonic acids showed3-5 that the yields of condensation