A valuable synthesis of reduced peptide bond by microwave irradiation

Vincenzo Santagada, Francesco Frecentese, Ferdinando Fiorino, Donatella Cirillo, Elisa Perissutti, Beatrice Severino, Sara Terracciano, Giuseppe Caliendo

Research output: Contribution to journalArticle

Abstract

Methyleneamine is a reduced form of the amide bond. The CH2NH group may be a useful tool for delineating important hydrogen-bonding points and may also offer a general strategy for the production of enzyme resistance and potent competitive antagonists. This paper describes a facile synthesis of the CH2NH group by application of microwave energy. Moreover the importance of sterically hindered amino acids as well as the electronic effects of the side chain, in the synthesis of the hydroxamate and in the reductive alkylation steps, are evaluated. Room temperature, conventional heating and microwave irradiation of the reactions are compared. Synthesis by microwave irradiation gave the desired compound in higher yields and in shorter reaction times than those obtained at room temperature.

Original languageEnglish
Pages (from-to)899-901
Number of pages3
JournalQSAR and Combinatorial Science
Volume23
Issue number10
DOIs
Publication statusPublished - Dec 2004

Keywords

  • Microwave irradiation
  • Surrogate peptide bond
  • Synthesis of CHNH group

ASJC Scopus subject areas

  • Discrete Mathematics and Combinatorics
  • Pharmacology

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    Santagada, V., Frecentese, F., Fiorino, F., Cirillo, D., Perissutti, E., Severino, B., Terracciano, S., & Caliendo, G. (2004). A valuable synthesis of reduced peptide bond by microwave irradiation. QSAR and Combinatorial Science, 23(10), 899-901. https://doi.org/10.1002/qsar.200420037