Synthesis and structure of oxetane containing tripeptide motifs

Abstract

A new class of peptidomimetic is reported in which one of the amide CO 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.