Stereochemical aspects of the bioreduction of the conjugated double bond of perillaldehyde (Articolo in rivista)

Type
Label
  • Stereochemical aspects of the bioreduction of the conjugated double bond of perillaldehyde (Articolo in rivista) (literal)
Anno
  • 2004-01-01T00:00:00+01:00 (literal)
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#doi
  • 10.1016/j.tetasy.2004.08.025 (literal)
Alternative label
  • Fronza Giovanni, Fuganti Claudio, Pinciroli Matteo, Serra Stefano (2004)
    Stereochemical aspects of the bioreduction of the conjugated double bond of perillaldehyde
    in Tetrahedron: asymmetry (Print)
    (literal)
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#autori
  • Fronza Giovanni, Fuganti Claudio, Pinciroli Matteo, Serra Stefano (literal)
Pagina inizio
  • 3073 (literal)
Pagina fine
  • 3077 (literal)
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#numeroVolume
  • 15 (literal)
Rivista
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#pagineTotali
  • 5 (literal)
Note
  • ISI Web of Science (WOS) (literal)
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#affiliazioni
  • CNR - ICRM Politecnico di Milano, Dipartimento di Chimica (literal)
Titolo
  • Stereochemical aspects of the bioreduction of the conjugated double bond of perillaldehyde (literal)
Abstract
  • A study on the regioselective reduction of the conjugate double bond of perillaldehyde is described. The chemical reduction of this substrate was investigated in order to provide a straightforward access to the relevant natural flavour, dihydroperill-aldehyde. The biological reduction of both natural (S)-(-)-perillaldehyde and synthetic (R)-(+)-perillaldehyde was accomplished by means of fermenting baker's yeast. The latter microorganism converted, with different diastereoselectivity, the (S)- and (R)-enantiomers into the corresponding trans and cis saturated alcohols, respectively. The origin of the hydrogen atoms added to the double bond was studied by deuterium labelling experiments and H-2 NMR measurements that clearly demonstrate a different mechanism of the biohydrogenation of the two enantiomeric forms of perillaldehyde. (literal)
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