Synlett 2003(9): 1344-1348
DOI: 10.1055/s-2003-40355
LETTER
© Georg Thieme Verlag Stuttgart ˙ New York

Deuterium-labeled 2′-Hydroxypyridoxol

Nisar Ullah, Johannes Zeidler, Ian D. Spenser*
Department of Chemistry, McMaster University, Hamilton, Ontario L8S 4M1, Canada
Fax: +1(905)5222509; e-Mail: spenser@mcmaster.ca;
Further Information

Publication History

Received 25 November 2002
Publication Date:
30 June 2003 (online)

Abstract

The preparation of [5′,5′-2H2]- and [2′,2′,5′,5′-2H4]-2′-hydroxypyridoxol, as well as of [5′,5′-2H2]-4-pyridoxic acid, starting from 3,4′-O-isopropylidenepyridoxol, is described. The labeled compounds were employed in an investigation of the biosynthesis of Vitamins B1 and B6.

    References

  • 1 Zeidler J. Ullah N. Gupta RN. Pauloski RM. Sayer BG. Spenser ID. J. Am. Chem. Soc.  2002,  124:  4542 
  • 2 Wu Y. Ahlberg P. Acta Chem. Scand.  1989,  43:  1009 
  • 3 Nelson JT. Nelson PH. Magn. Reson. Chem.  1987,  25:  309 
  • 4 Korytnyk W. Wiedeman W. J. Chem. Soc.  1962,  2531 
  • 5 Iwata M. Kuzuhara H. Bull. Chem. Soc. Jpn.  1985,  58:  2502 
  • 6 Korytnyk W. Paul B. J. Heterocycl. Chem.  1965,  2:  144 
  • 7 Korytnyk W. Kris EJ. Singh RP. J. Org. Chem.  1964,  29:  574 
  • 8 Argoudelis CJ. Kummerow FA. J. Org. Chem.  1964,  29:  2663 
  • 9 Tomita I. Brooks HG. Metzler DE. J. Heterocycl. Chem.  1966,  3:  178 
  • 10 Tazuya K. Azumi C. Yamada K. Kumaoka H. Vitamins (Japan)  1995,  69:  167 
  • 11 Coburn SP. Lin CC. Schaltenbrand WE. Mahuren JD. J. Labelled Compd. Radiopharm.  1982,  19:  703 
  • 12 Korytnyk W. Paul B. J. Heterocycl. Chem.  1965,  2:  481 
  • 13 Ahrens H. Korytnyk W. J. Heterocycl. Chem.  1967,  4:  625 
  • 14 Huff JW. Perlzweig WA. J. Biol. Chem.  1944,  155:  345 
  • 15 Korytnyk W. Srivastava SC. Angelino N. Potti PGG. Paul B. J. Med. Chem.  1973,  16:  1096 
  • 16 Agrawal KC. Clayman S. Sartorelli AC. J. Pharm. Sci.  1976,  65:  297 
  • 17 Bedford GR. Katritzky AR. Wuest HM. J. Chem. Soc.  1963,  4600