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Synthesis 2012(6): 862-864  
DOI: 10.1055/s-0031-1289689
SHORTPAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of a New Deuterium-Labeled Phytol as a Tool for Biosynthetic Studies

Lourdes Muñoz, Angel Guerrero*
Department of Biological Chemistry and Molecular Modeling, IQAC (CSIC), 08034 Barcelona, Spain
Fax: +34(93)2045904; e-Mail: angel.guerrero@iqac.csic.es;
Further Information

Publication History

Received 24 November 2011
Publication Date:
03 February 2012 (online)

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Abstract

An efficient and stereoselective synthesis of a new deuterium-labeled phytol as a useful tracer in biosynthetic processes is presented.

Key words

deuterium-labeled compounds - phytol - terpenoids - conjugate addition - natural products - biosynthesis

    References

  • 1 van den Brink DM. Wanders RJA. Cell. Mol. Life Sci.  2006,  63:  1752 
    Google Scholar
  • 2 Netscher T. Vitam. Horm.  2007,  76:  155 
    Google Scholar
  • 3 Daines AM. Payne RJ. Humphries ME. Abell AD. Curr. Org. Chem.  2003,  7:  1625 
    Google Scholar
  • 4 McGinty D. Letizia CS. Api AM. Food Chem. Toxicol.  2010,  48:  S59 
    Google Scholar
  • 5a Muralidharan FN. Muralidharan VB. Biochim. Biophys. Acta  1986,  883:  54 
    Google Scholar
  • 5b Poulter CD. Aoki T. Daniels L. J. Am. Chem. Soc.  1988,  110:  2620 
    Google Scholar
  • 6 Hanson JR. The Organic Chemistry of Isotopic Labeling   The Royal Society of Chemistry; Cambridge: 2011.  p.200 
    Google Scholar
  • 7a Emery VC. Akhtar M. Biochemistry  1987,  26:  1200 
    Google Scholar
  • 7b Samuel O. El Hachimi Z. Azerad R. Biochimie  1974,  56:  1279 
    Google Scholar
  • 7c Schulz S. Yildizhan S. van Loon JJA. J. Chem. Ecol.  2011,  37:  360 
    Google Scholar
  • 7d Urano S. Matsuo M. Heterocycles  1984,  22:  1975 
    Google Scholar
  • 8 Harwood LM. Casy G. Sherlock J. Synth. Commun.  1990,  20:  1287 
    Google Scholar
  • 9 MacCarthy ED. Calvin M. Tetrahedron  1967,  23:  2609 
    Google Scholar
  • 10a Hengartner U. Chougnet A. Liu K. Woggon WD. Chem. Eur. J.  2010,  16:  1306 
    Google Scholar
  • 10b Wang X.-Z. Wu Y.-L. Jiang S. Singh G. Tetrahedron Lett.  1999,  40:  8911 
    Google Scholar
  • 11 Silva I. Rocha SM. Coimbra MA. Marriott PJ. J. Chromatogr. A  2010,  1217:  5511 
    Google Scholar
  • 12 Havlik J. Kokoska L. Vasickova S. Valterova I. Flavour Fragr. J.  2006,  21:  713 
    Google Scholar