Issue 0, 1973

Polypeptides. Part XXIII. The synthesis of peptides of α-benzylphenylalanine by unconventional methods, with a note on magnetic non-equivalence in derivatives of α-benzylphenylalanine

Abstract

α-Benzylphenylalanine is best prepared by use of the Ugi four-component condensation method, followed by hydrolysis and hydrogenolysis of the intermediate N-acetyl-N,α-dibenzylphenylalanine. The same general procedure gives good yields of α-benzylphenylalanine peptides, but is limited in its application owing to the complete racemisation which attends the conversion of L-amino-acid esters into the isocyanides. The oxazolinone method is useful for the synthesis of peptides of α-benzylphenylalanine by the fragment condensation strategy employing small peptides containing C-terminal α-benzylphenylalanine residues, but breaks down with larger peptides.

Many, but not all, derivatives of α-benzylphenylalanine show magnetic non-equivalence of the benzyl methylene protons.

Article information

Article type
Paper

J. Chem. Soc., Perkin Trans. 1, 1973, 98-105

Polypeptides. Part XXIII. The synthesis of peptides of α-benzylphenylalanine by unconventional methods, with a note on magnetic non-equivalence in derivatives of α-benzylphenylalanine

H. L. Maia, B. Ridge and H. N. Rydon, J. Chem. Soc., Perkin Trans. 1, 1973, 98 DOI: 10.1039/P19730000098

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