User menu

Accès à distance ? S'identifier sur le proxy UCLouvain

Regioselective synthesis of 3-hydroxyorthanilic acid and its biotransformation into a novel phenoxazinone dye by use of laccase

Primary tabs

Bruyneel, Frédéric [UCL] Enaud, Estelle [UCL] Billottet, Ludovic [UCL] Vanhulle, Sophie [UCL] Marchand-Brynaert, Jacqueline [UCL]

A natural phenoxazinone derivative, cinnabarinic acid (2, CA, R = CO2H), could be obtained in vitro with the aid of purified laccase from the fungi Pycnoporus cinnabarinus by oxidative dimerization of 3-hydroxyanthranilic acid (1, 3-HAA, R = CO2H). With the aim of gaining access to a new class of water-soluble chromophores and potential bioactive molecules, the regioselective sulfonation of 2-hydroxyanihne was investigated. Straightforward insertion of a sulfonate group into a carbon-metal bond provided an efficient and selective process for the synthesis of 3-hydroxyorthanilic acid (3, 3-HOA, R = SO3H). This sulfonated compound was then subjected to laccase oxidation in order to mimic the cinnabarinic acid synthesis. A practical HPLC method to study the oxidized products was developed, and the major product of biotransformation - namely 2-aniino-3-oxo-3H-phenoxazin-1,9-disulfonic acid (4, LAO, R = SO3H) - was isolated and identified as the sulfonate analogue of cinnabarinic acid. ((c) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008).

Document type Article de périodique (Journal article) – Article de recherche
Publication date 2008
Language Anglais
Journal information "European Journal of Organic Chemistry" - no. 1, p. 70-79 (2008)
Peer reviewed yes
Publisher Wiley-v C H Verlag Gmbh (Weinheim)
issn 1434-193X
Publication status Publié
Affiliations UCL - SC/CHIM - Département de chimie
UCL - AGRO/CABI - Département de chimie appliquée et des bio-industries
Keywords laccase ; phenoxazinone ; lithiation ; biotransformation ; aromatic sulfonation reaction
Links
  1. Barry, Biochemistry, 28, 6323 (1989)
  2. Eggert, FEBS Lett., 376, 202 (1995)
  3. Osiadacz, J. Biotechnol., 72, 141 (1999)
  4. Jose, Tetrahedron, 62, 11021 (2006)
  5. Newton, Radiat. Phys. Chem., 75, 473 (2006)
  6. Gulston, Nucleic Acid Res., 32, 1602 (2004)
  7. , , , , WO2004067519, 2004 .
  8. , , , WO2003062213, 2003 .
  9. , EP159587##2, 2005 .
  10. Ruzika1, Monatsh. Chem., 98, 2185 (1967)
  11. Frade, Tetrahedron Lett., 46, 4949 (2005)
  12. Ho, Tetrahedron, 62, 578 (2006)
  13. Smith, J. Org. Chem., 61, 1530 (1996)
  14. Hajdok, Tetrahedron Lett., 48, 5073 (2007)
  15. Burton, Curr. Org. Chem., 7, 1317 (2003)
  16. Corey, Tetrahedron Lett., 32, 2857 (1991)
  17. Corey, J. Am. Chem. Soc., 111, 5493 (1989)
  18. Altenburger, Bioorg. Med. Chem., 12, 1713 (2004)
  19. Wang, Bioorg. Med. Chem. Lett., 17, 3864 (2007)
  20. McCleland, Bioorg. Med. Chem. Lett., 17, 1713 (2007)
  21. Allan Z. J., Podstata J., Aromatische diazo- und azoverbindungen LXXI. Darstellung von azofarbstoffen aus den sulfitaddukten des resorcins und aus phenol-m-sulfonsäre. Alkalische sulfitierung, 10.1135/cccc19664129
  22. Hofmann, Synthesis, 09, 699 (1979)
  23. Wuts, Synthesis, 1593 (1998)
  24. Macdonald, J. Chem. Soc. Chem. Commun., 1528 (1987)
  25. Rocca, J. Heterocycl. Chem., 32, 1171 (1995)
  26. Stanetty, J. Org. Chem., 62, 1514 (1997)
  27. Gilbert, Chem. Rev., 62, 549 (1962)
  28. Floyd, J. Org. Chem., 47, 5160 (1982)
  29. Weissman, Tetrahedron, 61, 7833 (2005)
  30. Kumar, Bioorg. Med. Chem., 10, 3997 (2002)
  31. Pettit, J. Org. Chem., 69, 2251 (2004)
  32. Iwahashi, J. Chromatogr., B: Biomed. Appl., 736, 237 (1999)
  33. MANTHEY M, PYNE S, TRUSCOTT R, Mchanism of reaction of 3-hydroxyanthranilic acid with molecular oxygen, 10.1016/0304-4165(90)90078-b
  34. Manthey, J. Heterocycl. Chem., 28, 1157 (1991)
  35. Manthey, J. Org. Chem., 53, 1486 (1988)
  36. Reemtsma, Trends Anal. Chem., 20, 500 (2001)
  37. Reemtsma, J. Chromatogr., A, 733, 473 (1996)
  38. Bailey, Chem. Commun., 408 (1967)
  39. Gottlieb, J. Org. Chem., 62, 7512 (1997)
  40. Organometallics in Synthesis. A Manual, 2nd ed., Chichester, 2002 .
  41. Dai, Tetrahedron, 51, 12263 (1995)
  42. Gribble, Tetrahedron, 27, 3785 (1971)
Bibliographic reference Bruyneel, Frédéric ; Enaud, Estelle ; Billottet, Ludovic ; Vanhulle, Sophie ; Marchand-Brynaert, Jacqueline. Regioselective synthesis of 3-hydroxyorthanilic acid and its biotransformation into a novel phenoxazinone dye by use of laccase. In: European Journal of Organic Chemistry, no. 1, p. 70-79 (2008)
Permanent URL http://hdl.handle.net/2078.1/36862