α hydroxylation of carboxylic acids with molecular oxygen catalyzed by the α oxidase of peas (Pisum sativum): A novel biocatalytic synthesis of enantiomerically pure (R)-2-hydroxy acids

Journal of the American Chemical Society

Volumn 120, Issue 43, 1998, Pages 11044-11048

  Adam, Waldemar ^a   Boland, Wilhelm ^b   Hartmann Schreier, Jenny ^a   Humpf, Hans Ulrich ^a   Lazarus, Michael ^a   Saffert, Alexander ^a   Saha Möller, Chantu R ^a   Schreier, Peter ^a  

^a UNIVERSITY OF WÜRZBURG   (Germany)

^b MAX PLANCK INSTITUTE FOR CHEMICAL ECOLOGY   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

2 HYDROXY FATTY ACID DERIVATIVE; CARBOXYLIC ACID; OXIDOREDUCTASE; OXYGEN; SULFUR; UNCLASSIFIED DRUG;

ARTICLE; BIOTRANSFORMATION; CATALYSIS; CHEMICAL BOND; CIRCULAR DICHROISM; CONTROLLED STUDY; ENANTIOMER; ENZYME SPECIFICITY; GAS CHROMATOGRAPHY; HYDROXYLATION; NONHUMAN; OXIDATION; PEA; PLANT LEAF; STEREOCHEMISTRY;

PISUM SATIVUM;

EID: 0032483752     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja981252r     Document Type: Article

References (36)

1. Hitchcock, C.; James, A. T. Biochim. Biophys. Acta 1966, 116, 413-424.
2. Shine, W. E.; Stumpf, P. K. Arch. Biochem. Biophys. 1974, 162, 147-157.
3. Galliard, T.; Matthew, J. A. Biochim. Biophys. Acta 1976, 424, 26-35.
4. Laties, G. G.; Hoelle, C. Phytochemistry 1967, 6, 49-57.
5. Kajiwara, T.; Yoshikawa, H.; Saruwatari, T.; Hatanaka, A.; Kawai, T.; Ishihara, M.; Tsuneya, T. Phytochemistry 1988, 27, 1643-1645.
6. (a) Salim-Hanna, M.; Campa, A.; Cilento, G. Photochem. Photobiol. 1987, 45, 849-854.
7. (b) Campa, A.; Salim-Hanna, M.; Cilento, G. Photochem. Photobiol. 1989, 49, 349-354.
8. Schuster, G. B. Acc. Chem. Res. 1979, 12, 366-373.
9. (a) Morris, L. J.; Hitchcock, C. Eur. J. Biochem. 1968, 4, 146-148.
10. (b) Hitchcock, C.; Rose, A. Biochem. J. 1971, 125, 1155-1156.
11. (c) Markovetz, A. J.; Stumpf, P. K.; Hammarström, S. Lipids 1972, 7, 159-164.
12. (a) Prelog, V.; Wilhelm, M.; Bright, D. B. Helv. Chim. Acta 1954, 37, 221-224.
13. (b) Lee, J. B.; Downie, I. M. Tetrahedron 1967, 23, 359-363.
14. (c) Mori, K.; Takigawa, T.; Matsuo, T. Tetrahedron 1979, 35, 933-940.
15. (a) Evans, D. A.; Morrissey, M. M.; Dorow, R. L. J. Am. Chem. Soc. 1985, 107, 4346-4348.
16. (b) Corey, E. J.; Link, J. O.; Shao, Y. Tetrahedron Lett. 1992, 33, 3435-3438.
17. (a) Wong, C.-H.; Matos, J. R. J. Org. Chem. 1985, 50, 1992-1994.
18. (b) Nakamura, K.; Inoue, K.; Ushio, K.; Oka, S.; Ohno, A. J. Org. Chem. 1988, 53, 2589-2593.
19. (c) Effenberger, F. Angew. Chem. 1994, 106, 1609-1619.
20. (d) Sugai T.; Ohta, H. Tetrahedron Lett. 1991, 32, 7063-7064.
21. (e) Adam, W.; Lazarus, M.; Boss, B.; Saha-Möller, C. R.; Humpf, H.-U.; Schreier, P. J. Org. Chem. 1997, 62, 7841-7843.
22. (f) Adam, W.; Fell, R. T.; Hoch, U.; Saha-Möller, C. R.; Schreier, P. Tetrahedron: Asymmetry 1995, 6, 1047-1050.
23. Adam, W.; Lazarus, M.; Saha-Möller, C. R.; Schreier, P. Tetrahedron: Asymmetry 1997, 7, 2287-2292.
24. Kajiwara, T.; Matsui, K.; Akakabe, Y. In Biotechnology for Improved Foods and Flavours; Takeoaka, G. R., Teranishi, R., Williams, P. J., Kobayashi, A., Eds.; American Chemical Society: Washington, 1996; pp 146-166.
25. Koljak, R.; Boutaud, O.; Shieh, B.-H.; Samel, N.; Brash, A. R. Science 1997, 277, 1994-1996.
26. Kagan, H. B. In Catalytic Asymmetric Synthesis; Ojima, I., Ed.; VCH Publishers: New York, 1993; pp 203-226.
27. Dale, J. A.; Dull, D. L.; Mosher, H. S. J. Org. Chem. 1969, 34, 2543-2549.
28. Rees, L.; Suckling, C. J.; Wood, H. C. S. J. Chem. Soc., Chem. Commun. 1987, 470-472.
29. Adam, W.; Lazarus, M.; Schmerder, A.; Humpf, H.-U.; Saha-Möller, C. R.; Schreier, P. Eur. J. Org. Chem. 1998, 2013-2018.
30. Hamberg, M. Anal. Biochem. 1971, 43, 515-526.
31. Nakanishi, K.; Berova, N. In Circular Dichroism. Principles and Applications; Nakanishi, K., Berova, N., Woody, R. W., Eds; VCH Publishers: New York, 1994; pp 361-398.
32. (a) Gimple, O.; Schreier, P.; Humpf, H.-U. Tetrahedron: Asymmetry 1997, 8, 11-14.
33. (b) Hör, K.; Gimple, O.; Schreier, P.; Humpf, H.-U. J-Org. Chem. 1998, 63, 322-325.
34. 3CN).
35. Andersen Borge, G. I.; Slinde, E.; Nilsson, A. Biochim. Biophys. Acta 1997, 1344, 47-58.
36. Horn, D. H. S.; Hougen, F. W.; von Rudloff, E.; Sutton, D. A. J. Chem. Soc. 1954, 177-180.