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Synfacts 2005(1): 0176-0176  
DOI: 10.1055/s-2005-916001
Polymer-Supported Synthesis
© Georg Thieme Verlag Stuttgart · New York

Proline Editing: A New Strategy for the Diversity-Oriented Peptide Synthesis

Contributor(s): Yasuhiro Uozumi, Masahiro Kimura
K. M. Thomas, D. Naduthambi, G. Tririya, N. J. Zondlo*
University of Delaware, USA
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Publication History

Publication Date:
21 September 2005 (online)

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Significance

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.