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Issue 63, 2014
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Synthesis and structure of oxetane containing tripeptide motifs

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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 NZ 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

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Article information


Submitted
09 May 2014
Accepted
16 Jun 2014
First published
17 Jun 2014

Chem. Commun., 2014,50, 8797-8800
Article type
Communication

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

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