The Arndt-Eistert Reaction in Peptide Chemistry: A Facile Access to Homopeptides

摘要

beta-Amino acids, though less abundant than a-amino acids, are components of natural peptides. In recent years their importance for the preparation of modified peptides and (Madam antibiotics has increased enormously. Quite a number of methods for thesynthesis of enantiopure beta-amino acids exists already. Still it would be a conceptually new. simple approach for the construction of peptides containing beta-amino acids, if the generation of the beta-amino acid moiety could be combined with a peptide coupling step. To this end. we have now applied to peptides the chain extension of carboxylic acids developed by Arndt and Eistert. When we started this work, it was not certain whether the peptidic ketenes A formed in this reaction could be trapped intennolecularly. and if so. whether they would couple selectively with the free amino function of a second peptide.