Synthesis of enantiomerically pure cis- and trans-4-amino-1-oxyl-2,2,6,6-tetramethylpiperidine-3-carboxylic acid: a spin-labelled, cyclic, chiral beta-amino acid, and 3D-structural analysis of a doubly spin-labelled beta-hexapeptide (Articolo in rivista)

Type
Label
  • Synthesis of enantiomerically pure cis- and trans-4-amino-1-oxyl-2,2,6,6-tetramethylpiperidine-3-carboxylic acid: a spin-labelled, cyclic, chiral beta-amino acid, and 3D-structural analysis of a doubly spin-labelled beta-hexapeptide (Articolo in rivista) (literal)
Anno
  • 2007-01-01T00:00:00+01:00 (literal)
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#doi
  • 10.1002/ejoc.200700153 (literal)
Alternative label
  • K. Wright, M. Sarciaux, A. de Castries, M. Wakselman, J.P. Mazaleyrat, A. Toffoletti, C. Corvaja, M. Crisma, C. Peggion, F. Formaggio, C. Toniolo (2007)
    Synthesis of enantiomerically pure cis- and trans-4-amino-1-oxyl-2,2,6,6-tetramethylpiperidine-3-carboxylic acid: a spin-labelled, cyclic, chiral beta-amino acid, and 3D-structural analysis of a doubly spin-labelled beta-hexapeptide
    in European journal of organic chemistry (Print)
    (literal)
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#autori
  • K. Wright, M. Sarciaux, A. de Castries, M. Wakselman, J.P. Mazaleyrat, A. Toffoletti, C. Corvaja, M. Crisma, C. Peggion, F. Formaggio, C. Toniolo (literal)
Pagina inizio
  • 3133 (literal)
Pagina fine
  • 3144 (literal)
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  • Citazioni WOS: 6 Impact Factor 2007: 2.914 Coautore (literal)
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  • - (literal)
Rivista
Note
  • ISI Web of Science (WOS) (literal)
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#affiliazioni
  • ILV, UMR CNRS 8180, University of Versailles, 78035 Versailles, France; Institute of Biomolecular Chemistry, Padova Unit, CNR, Department of Chemistry, University of Padova, 35131 Padova, Italy (literal)
Titolo
  • Synthesis of enantiomerically pure cis- and trans-4-amino-1-oxyl-2,2,6,6-tetramethylpiperidine-3-carboxylic acid: a spin-labelled, cyclic, chiral beta-amino acid, and 3D-structural analysis of a doubly spin-labelled beta-hexapeptide (literal)
Abstract
  • Amination of 3-carboxymethyl-l-oxyl-2,2,6,6-tetramethyl-4-piperidone (1) with either (R)- or (S)-alpha,-methylbenzylamine gave corresponding enamines 2. Whereas the reduction with. NaBH3CN/CH3COOH afforded predominantly a mixture of two possible cis diastereomers of 3, (1'R,3S,4S)1(1'R,3R,4R) or (VS,3R,4R)1(l'S,3S,4S), which could be separated by crystallisation of their HCl salts, the use of NaBH4/(CH3)(2)-HCOOH as the reducing agent resulted in a mixture of one trans- and one cis diastereomer of 3 (1'R,3S,4R)1(l'R,3R,4R) or (l'S,3R,4S)1(l'S,3S,4S) in varying proportions depending upon the conditions used. The stereochemistry of the four diastereomers of 3 was clearly established by X-ray diffraction analysis of one of them, combined with H-1 NMR spectroscopic studies after nitroxide reduction. Removal of the chiral auxiliary from the separated diastereomers of 3 by hydrogenation and regeneration of the nitroxide radical gave expected amino esters 4. A model beta-hexapeptide containing (3R,4S)beta-TOAC combined with (1S,2S)-2-aminocyclohexane carboxylic acid was synthesised by solution methods and its preferred conformation (3(14)-helix) was assessed by FTIR absorption, CD, and EPR spectroscopy. (literal)
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