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Synlett 1997; 1997(1): 63-65
DOI: 10.1055/s-1997-706
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The Synthesis of Conformationally Constrained Peptides and Pseudo-Peptides Incorporating an Endo-(2S,3R)-2-Amino-3-Carboxy-Norborn-5-ene Residue

Iwan G. Jones1 , Wyn Jones2 , Michael North3
  • 1Department of Chemistry, University of Wales, Bangor, Gwynedd, LL57 2UW
  • 2Peboc Division of Eastman Chemical (UK) Ltd., Industrial Estate, Llangefni, Anglesey, Gwynedd, LL77 7YQ
  • 3Department of Chemistry, University of Wales, Bangor, Gwynedd, LL57 2UW, Email m.north@bangor.ac.uk
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Publikationsdatum:
22. März 2004 (online)

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Methodology has been developed to carry out a Curtius rearrangement on enantiomerically pure amido-acids derived from (S)-proline esters. The resulting isocyanates were used to prepare conformationally constrained peptides incorporating and endo-(2S,3R)-2-amino-3-carboxy-norborn-5-ene residue.

endo-(2S, 3R)-2-amino-3-carboxy-norborn-5-ene - proline - peptide - Curtius-rearrangement - isocyanate