Issue 63, 2014

Synthesis and structure of oxetane containing tripeptide motifs

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

Supplementary files

Article information

Article type
Communication
Submitted
09 ⵎⴰⵢ 2014
Accepted
16 ⵢⵓⵏ 2014
First published
17 ⵢⵓⵏ 2014

Chem. Commun., 2014,50, 8797-8800

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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