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Synlett 1999; 1999(S1): 994-996
DOI: 10.1055/s-1999-3115
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Synthesis and Conformation of a Novel Dipeptide Derived from a γ-Amino Acid with Norbornane Skeleton

Jörn Duwenhorst* , Franz-Peter Montforts
  • *Institut für Organische Chemie, FB 2, Universität Bremen, Leobener Strasse NW 2 C, D-28359 Bremen, Germany; Fax +49(4 21)2 18 37 20; E-mail: mont@chemie.uni-bremen.de
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Publication Date:
31 December 1999 (online)

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An enantiomerically pure γ-amino acid 9 with norbornane skeleton was synthesized from the norbornene dicarboxylic acid 5. NOE studies and AM1 calculations on the protected dipeptide 10 derived from this amino acid revealed that the conformation of the peptide backbone is determined by an intramolecular hydrogen bond between the two subunits.

γ-amino acids - γ-dipeptide conformation - norbornane