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- Title
Synthesis and Crystal Structure of Peptide-2,2′-Biphenyl Hybrids.
- Authors
Mann, Enrique; Montero, Ana; Maestro, Miguel A.; Herradón, Bernardo
- Abstract
1,1′-Biphenyl derivatives with amino acid/peptide substitution at C(2) and C(2′) (' peptide-biphenyl hybrids', 6- 8) have been prepared by direct N-acylation of amino acid/peptide derivatives with 1,1′-biphenyl-2,2′-dicarbonyl dichloride ( 5). Both conformers, which arise from the rotation around the arylaryl bond, have been detected by 1H-NMR spectroscopy. Single atropisomers of each 6 (( R)-configuration at the stereogenic axis) and 7 (( S)-configuration at the stereogenic axis) have been obtained in quantitative yield by slow evaporation of methanolic solutions. The procedures are dynamic atropselective resolutions ( asymmetric transformations of the second kind). The crystal structures of the peptide-biphenyl hybrids 6 and 7 show highly ordered molecular and supramolecular structures with extensive intramolecular and intermolecular H-bonding.
- Publication
Helvetica Chimica Acta, 2002, Vol 85, Issue 11, p3624
- ISSN
0018-019X
- Publication type
Article
- DOI
10.1002/1522-2675(200211)85:11<3624::AID-HLCA3624>3.0.CO;2-Y