In vitro condensation of amino acids in aqueous media: A synthesis driven by catalytic carbon monoxide oxidation

Joseph E. Remias, Christine Elia, Laurie E. Grove, Ayusman Sen

Research output: Contribution to journalArticle

2 Scopus citations

Abstract

A novel mechanism is proposed for amino acid condensations to oligopeptides in aqueous media. The palladium-catalyzed condensation appears to proceed through a mechanism involving the Pd(0)/Pd(II) redox cycle. The reaction requires the use of carbon monoxide and an oxidant, and it is proposed that the oxidation of carbon monoxide to carbon dioxide drives the otherwise thermodynamically uphill condensation. The reaction occurs for several amino acids including glycine, alanine, β-alanine, and 5-aminopentanoic acid. Competition studies between glycine and alanine reveal steric effects on product formation. Dipeptides are the predominant condensation products, though some longer chains, containing up to 4 amino acids, can be observed. First-order plots for dipeptide appearance show an inverse, secondary, isotope effect consistent with the rate determining carboxylic-carbamic anhydride formation.

Original languageEnglish (US)
Pages (from-to)2956-2965
Number of pages10
JournalInorganica Chimica Acta
Volume359
Issue number9
DOIs
StatePublished - Jun 1 2006

All Science Journal Classification (ASJC) codes

  • Physical and Theoretical Chemistry
  • Inorganic Chemistry
  • Materials Chemistry

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