Proline Editing: A New Strategy for the Diversity-Oriented Peptide Synthesis
K. M. Thomas, D. Naduthambi, G. Tririya, N. J. Zondlo*
University of Delaware, USA
21 September 2005 (online)
Conformationally diverse peptides containing 4-substituted proline residues a-g were synthesized from inexpensive Fmoc-trans-hydroxyproline via post-synthetic modification. Peptide A containing a trans-hydroxyproline residue was easily transformed into peptides a-g through several reaction sequences using DAST, PDC, and/or Mitsunobu conditions on the solid-support followed by the standard cleavage from the resin. Conformational properties of these peptides were also studied by NMR.