Formation of acyclic α- and γ-ketols and 12-oxophytodienoic acid from linolenic acid 13-hydroperoxide by a flax enzyme preparation. Evidence for a single enzyme leading to a common allene epoxide intermediate

Journal of the Chemical Society, Chemical Communications

Volumn , Issue 8, 1988, Pages 558-560

  Crombie, Leslie ^a   Morgan, David O ^a  

^a UNIVERSITY OF NOTTINGHAM   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 37049084892     PISSN: 00224936     EISSN: None     Source Type: Journal    
DOI: 10.1039/C39880000558     Document Type: Article

References (28)

1. D. C. Zimmerman, Biochem. Biophys. Res. Commun., 1966, 23, 398
2. D. C. Zimmerman and B. Vick, Plant Physiol., 1970, 46, 445
3. D. C. Zimmerman and P. Feng, Lipids, 1978, 13, 313
4. D. C. Zimmerman and P. Feng, Lipids, 1979, 14, 710
5. B. A. Vick and D. C. Zimmerman, Plant Physiol., 1979, 63, 490
6. P. Feng, B. A. Vick, andD. C. Zimmerman, Lipids, 1981,16, 377.
7. B. A. Vick and D. C. Zimmerman, Plant Physiol., 1979, 64, 203
8. B. A. Vick and D. C. Zimmerman, Plant Physiol., 1986, 80, 202.
9. 'Natural Products Chemistry,' vol. 2, eds. K. Nakanishi, T. Goto, S. Ito, S. Natori, and S. Nozoe, Academic Press, New York, 1975
10. A. Mitra, 'The Synthesis of Prostaglandins,' Wiley, New York, 1977.
11. D. C. Zimmerman and B. Vick, Lipids, 1969, 5, 392. Evidence of 12-hydroperoxide has also been found, under certain circumstances, in our laboratory, E. Smith, personal communication.
12. J. G. Atkinson, D. W. Cillis, and R. S. Stuart, Can. J. Chem., 1969, 47, 477.
13. J. M. Osbond, P. G. Philpott, and J. C. Wickens, J. Chem. Soc, 1961, 2779.
14. D. S. Sgoutas, H. Sanden, and E. M. Young, J. Lipid Res., 1969, 10, 642.
15. B. A. Vick, P. Feng and D. C. Zimmerman, Lipids, 1980,15,468.
16. E. J. Corey, P. T. Lansbury Jr., and Y. Yamada, Tetrahedron Lett., 1985, 26, 4171
17. E. J. Corey and S. P. Matsuda, Tetrahedron Lett., 1987, 28, 4247
18. E. J. Corey, M. d'Alarco, S. P. T. Matsuda, P. T. Lansbury Jr., and Y. Yamada, J. Am. Chem. Soc, 1987, 109, 289.
19. E. J. Corey, K. Ritter, M. Yus, and C. Najera, Tetrahedron Lett., 1987, 3547.
20. J. Grimaldi and M. Bertrand, Tetrahedron Lett., 1969, 3269
21. J. Grimaldi and M. Bertrand, Bull. Soc. Chim. Fr., 1971, 957.
22. L. Crombie and D. O. Morgan, J. Chem. Soc, Chem. Commun., 1987, 503, and references cited therein.
23. L. Crombie and D. O. Morgan, J. Chem. Soc, Chem. Commun., 1988, preceding communication, and references cited therein.
24. B. A. Vick and D. C. Zimmerman, Plant Physiol., 1981, 67, 92.
25. T. Galliard and D. R. Phillips, Biochem. J., 1972, 129, 743
26. T. Galliard, D. R. Phillips, and D. J. Frost, Chem. Phys. Lipids, 1973, 11, 173.
27. L. Crombie, D. O. Morgan, and E. H. Smith, J. Chem. Soc, Chem. Commun., 1986, 502.
28. T. Galliard, D. A. Phillips, and J. A. Matthew, Biochem. Biophys. Acta, 1975, 409, 157.