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Synthesis and Crystal Structure of Peptide‐2,2′‐Biphenyl Hybrids
Author(s) -
Mann Enrique,
Montero Ana,
Maestro Miguel A.,
Herradón Bernardo
Publication year - 2002
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/1522-2675(200211)85:11<3624::aid-hlca3624>3.0.co;2-y
Subject(s) - chemistry , stereocenter , biphenyl , atropisomer , peptide , intramolecular force , stereochemistry , supramolecular chemistry , aryl , crystal structure , crystallography , organic chemistry , catalysis , alkyl , biochemistry , enantioselective synthesis
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 1 H‐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.