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 journalArticlepeer-review

    12 Citations (Scopus)
    32 Downloads (Pure)

    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

    Bibliographical note

    Copyright the Publisher 2017. Version archived for private and non-commercial use with the permission of the author/s and according to publisher conditions. For further rights please contact the publisher.

    Keywords

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

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