Reactivity of dehydroaspartic acid derivatives under peptide coupling conditions

Nalin L. Subasinghe, Rodney L. Johnson

Research output: Contribution to journalArticlepeer-review

Abstract

The reactivity of α-carboxy-activated dehydroaspartic acid derivativs with various N- and O-nucleophiles is described for the first time. Reaction of amino acid derivatives with Ac-ΔZAsp(OBut)-OH (4a) under a variety of coupling conditions gave very poor yields of the resulting dehydroasparyl dipeptides, while the coupling of 4a with oxygen nucleophiles gave very good yields of the dehydroaspartyl esters. In contrast, the coupling of amino acids with Cbz-ΔZAsp(OBut)-OH (4b) gave good yields of dehydroaspartyl dipeptides. The formaton of a highly reactive oxazolone intermediate is proposed to explain the low yields of peptide coupling between 4a and amino acids.

Original languageEnglish (US)
Pages (from-to)2649-2652
Number of pages4
JournalTetrahedron Letters
Volume33
Issue number19
DOIs
StatePublished - May 5 1992

Keywords

  • Dehydroaspartic acid
  • active ester
  • oxazolone
  • peptide coupling

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