Synthesis and application of photoproline-a photoactivatable derivative of proline

Abstract

A convenient synthesis is described of a derivative of L-proline called photoproline, containing a diazirine group at position-4 of the pyrrolidine ring, starting from L-4-hydroxyproline. The use of Fmoc-L-photoproline in the synthesis of a cyclic peptidomimetic antibiotic demonstrates that this photoprobe can be incorporated into synthetic peptides using solid-phase Fmoc chemistry. Photoproline may be of wide value in the preparation of diverse peptide-based photoaffinity probes. © RKAT-USA, Inc.