Jump to main content
Jump to site search
Publishing
Advanced

Issue 63, 2014
Previous Article Next Article

Synthesis and structure of oxetane containing tripeptide motifs

Nicola H. Powell,a  Guy J. Clarkson,a  Rebecca Notman,a  Piotr Raubo,b  Nathaniel G. Martinb  and  Michael Shipman*a 
Author affiliations

* Corresponding authors

a Department of Chemistry, University of Warwick, Gibbet Hill Road, Coventry, UK
E-mail: m.shipman@warwick.ac.uk
Fax: +44 2476 524112
Tel: +44 2476 523186

b AstraZeneca, Mereside, Alderley Park, Macclesfield, UK

Abstract

A new class of peptidomimetic is reported in which one of the amide C[double bond, length as m-dash]O bonds of the peptide backbone is replaced by an oxetane ring. They are synthesised by conjugate addition of various α-amino esters to a 3-(nitromethylene)oxetane, reduction of the nitro group and further coupling with N–Z protected amino acids to grow the peptide chain. Structural insights are provided by X-ray diffraction and molecular dynamics simulations.

Graphical abstract: Synthesis and structure of oxetane containing tripeptide motifs

Back to tab navigation
Please wait while Download options loads

Supplementary files

Publication details

The article was received on 09 May 2014, accepted on 16 Jun 2014 and first published on 17 Jun 2014


Article type: Communication
DOI: 10.1039/C4CC03507K
Citation: Chem. Commun., 2014,50, 8797-8800
  •   Request permissions ⌄

    Synthesis and structure of oxetane containing tripeptide motifs

    N. H. Powell, G. J. Clarkson, R. Notman, P. Raubo, N. G. Martin and M. Shipman, Chem. Commun., 2014, 50, 8797
    DOI: 10.1039/C4CC03507K

    If you are not the author of this article and you wish to reproduce material from it in a third party non-RSC publication you must formally request permission using RightsLink. Go to our Instructions for using RightsLink page for details.

    Authors contributing to RSC publications (journal articles, books or book chapters) do not need to formally request permission to reproduce material contained in this article provided that the correct acknowledgement is given with the reproduced material.

    Reproduced material should be attributed as follows:

    • For reproduction of material from NJC:
      Reproduced from Ref. XX with permission from the Centre National de la Recherche Scientifique (CNRS) and The Royal Society of Chemistry.
    • For reproduction of material from PCCP:
      Reproduced from Ref. XX with permission from the PCCP Owner Societies.
    • For reproduction of material from PPS:
      Reproduced from Ref. XX with permission from the European Society for Photobiology, the European Photochemistry Association, and The Royal Society of Chemistry.
    • For reproduction of material from all other RSC journals and books:
      Reproduced from Ref. XX with permission from The Royal Society of Chemistry.

    If the material has been adapted instead of reproduced from the original RSC publication "Reproduced from" can be substituted with "Adapted from".

    In all cases the Ref. XX is the XXth reference in the list of references.

    If you are the author of this article you do not need to formally request permission to reproduce figures, diagrams etc. contained in this article in third party publications or in a thesis or dissertation provided that the correct acknowledgement is given with the reproduced material.

    Reproduced material should be attributed as follows:

    • For reproduction of material from NJC:
      [Original citation] - Reproduced by permission of The Royal Society of Chemistry (RSC) on behalf of the Centre National de la Recherche Scientifique (CNRS) and the RSC
    • For reproduction of material from PCCP:
      [Original citation] - Reproduced by permission of the PCCP Owner Societies
    • For reproduction of material from PPS:
      [Original citation] - Reproduced by permission of The Royal Society of Chemistry (RSC) on behalf of the European Society for Photobiology, the European Photochemistry Association, and RSC
    • For reproduction of material from all other RSC journals:
      [Original citation] - Reproduced by permission of The Royal Society of Chemistry

    If you are the author of this article you still need to obtain permission to reproduce the whole article in a third party publication with the exception of reproduction of the whole article in a thesis or dissertation.

    Information about reproducing material from RSC articles with different licences is available on our Permission Requests page.

Search articles by author