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Triphenylphosphonio-acetyl-(Tpa)-amino acids (5) and peptide esters (6) are prepared from the corresponding monpchloro acetyl derivatives (3) and (4). Alternatively the Tpa- amino acids (5) may be obtained by treatment of the N-silyl amino acid silylesters with the triphenylphosphonio-acetic acid phenylester (7) or the corresponding ylide (8). Tpa- amino acids prepared in this manner may be used for peptide condensation. The Tpa- group is acid-stable. In aprotic media the ylides of the Tpa-dipeptide esters (13) are formed on treatment with strong bases, and are converted in the course of the Wittig- olefination to the substituted acrylo peptide esters 15. The trans o-nitro-cinnamoyl moiety may be cleaved from the amino function of the peptide esters as 3,4-dihydro-a- quinolone via catalytic hydrogenation.

Synthese und Reaktionen von Phosphonio-acetyl-Peptiden und ihren Yliden / Synthesis and Reactions of Phosphonio-acetyl Peptides and Ylides