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
- 1 January 1973
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- p. 98-105
- https://doi.org/10.1039/p19730000098
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.Keywords
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