130681-69-5Relevant academic research and scientific papers
Synthesis and spectroscopic properties of 14-, 15-, 15'- and 14'-monodeutero- and 15,15'-dideuterospheroidenes
Gebhard, R.,Dijk, J. T. M. van,Boza, M. V. T. J.,Hoef, K. van der,Lugtenburg, J.
, p. 332 - 341 (2007/10/02)
The high-yield synthesis of four mono- and one dideutero-labelled spheroidene, the carotenoid bound in the reaction centre of Rhodobacter sphaeroides 2.4.1, is described.The all-E isomers (14'-2H)-, (15'-2H)-, (15-2H)-, (14-2H)- and (15,15'-2H2)spheroidenes have been prepared in high purity with more than 95percent 2H incorporation from C(2)H3CN and/or Dibal-(2)H.The spectroscopic properties of the labelled compounds are discussed; the mass spectra reveal that toluene elimination from spheroidene is restricted to a single location in the molecule.
Synthesis and spectroscopy of (14'-13C)- and (15'-13C)spheroidene
Gebhart, R.,Hoef, K. van der,Lefeber, A. W. M.,Erkelens, C.,Lugtenburg, J.
, p. 378 - 387 (2007/10/02)
The preparation of two 13C-labelled isotopomers of spheroidene, the carotenoid bound in the photosynthetic reaction center of Rhodobacter sphaeroides, is described.All-E (14'-13C)-spheroidene has been synthesized in high yield and purity and with more than 98percent 13C incorporation starting from (2-13C)acetonitrile; similarly, all-E (15'-13C)spheroidene has been obtained starting from (1-13C)-acetonitrile.The spectroscopic properties of all-E spheroidene and its (14'-13C)- and (15'-13C)isotopomers are discussed.The mass spectra of the labelled compounds reveal that toluene is eliminated mainly from the central part of the molecule.Analysis of the 1H-NMR spectrum of all-E (15'-13C)spheroidene gives a value of 14.0 Hz for the 1H-1H coupling constant of the 15-15'double bond.
