Cyclization of linear tetrapeptides containing N-nethylated amino acids by using 1-propanephosphonic acid anhydride

Shengping Zhang, Luis M. De Leon Rodriguez, Ernest Lacey, Andrew M. Piggott, Ivanhoe K. H. Leung, Margaret A. Brimble*

*Corresponding author for this work

Research output: Contribution to journalArticle

9 Citations (Scopus)

Abstract

The cyclization of the linear tetrapeptides sequence H-NMePhe-Xaa1-NMePhe-Xaa2-OH (for which Xaa1 = Xaa2 = Ile, Val, or Leu; Xaa1 = Val; Xaa2 = Ile or Leu) by using 1-propanephosphonic acid anhydride was explored. An unanticipated finding is the cyclization towards cyclotetrapeptide conformers (kinetic products) that were highly prone to hydrolysis and that slowly interconvert into the more stable trans,cis,trans,cis (tctc) conformers (thermodynamic products).

Original languageEnglish
Pages (from-to)149-158
Number of pages10
JournalEuropean Journal of Organic Chemistry
Volume2017
Issue number1
DOIs
Publication statusPublished - 3 Jan 2017

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Keywords

  • Cyclization
  • Tetrapeptides
  • Conformation analysis
  • Natural products
  • Biological activity

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