A new bicyclic Dipeptide Isostere with Pyrrolizidinone Skeleton (Articolo in rivista)

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  • A new bicyclic Dipeptide Isostere with Pyrrolizidinone Skeleton (Articolo in rivista) (literal)
Anno
  • 2005-01-01T00:00:00+01:00 (literal)
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#doi
  • 10.1021/jo0487658 (literal)
Alternative label
  • Cordero Franca Maria; Pisaneschi Federica; Batista Meschini Karina; Valenza Silvia; Machetti Fabrizio; Brandi Alberto (2005)
    A new bicyclic Dipeptide Isostere with Pyrrolizidinone Skeleton
    in Journal of organic chemistry; ACS, American chemical society, Washington, DC (Stati Uniti d'America)
    (literal)
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#autori
  • Cordero Franca Maria; Pisaneschi Federica; Batista Meschini Karina; Valenza Silvia; Machetti Fabrizio; Brandi Alberto (literal)
Pagina inizio
  • 856 (literal)
Pagina fine
  • 867 (literal)
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#url
  • http://pubs.acs.org/doi/full/10.1021/jo0487653 (literal)
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#numeroVolume
  • 70 (literal)
Rivista
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  • 12 (literal)
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  • 3 (literal)
Note
  • Scopus (literal)
  • PubMe (literal)
  • ISI Web of Science (WOS) (literal)
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#affiliazioni
  • Istituto di Chimica dei Composti Organo metallici del CNR Dipartimento di Chimica Organica Ugo Schiff dell'Università di Firenze (literal)
Titolo
  • A new bicyclic Dipeptide Isostere with Pyrrolizidinone Skeleton (literal)
Abstract
  • The synthesis of a new conformationally constrained Gly-(s-cis)Pro Turn Mimetic (GPTM) in both racemic and enantiomerically pure forms and their incorporation into peptides 18, 21, and 24 are reported. The synthetic strategy adopted to assemble the bicyclic pyrrolizidinone skeleton is based on the 1,3-dipolar cycloaddition of the cyclic nitrone 4a derived from proline and acrylamide, followed by a reductive cleavage/cyclization domino process. The enantiomerically pure GPTMs are obtained by synthesis and separation of diastereomeric intermediates containing (1R)-1-phenylethylamine as chiral auxiliary. Analysis of pseudotripeptides 18, 21, and 22 by FT-IR and NMR shows that the amide proton of GPTM derivatives 21 is intramolecularly hydrogen bonded in CDCl3, while DMSO was shown to disrupt this hydrogen bond. (literal)
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