A model study on the mechanism of inhibition of fatty acyl desaturases by cyclopropene fatty acids

Tetrahedron

Volumn 54, Issue 34, 1998, Pages 10187-10198

  Quintana, Jordi ^a   Barrot, Mireia ^a   Fabrias, Gemma ^a   Camps, Francisco ^a  

^a DEPT OF ENVIRONMENTAL CHEMISTRY   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

ACYL COENZYME A DESATURASE; CYCLOPROPANE DERIVATIVE;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL REACTION; CHROMATOGRAPHY; ENZYME ACTIVE SITE; ENZYME ANALYSIS; ENZYME INHIBITION; ENZYME STRUCTURE; NUCLEAR OVERHAUSER EFFECT; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY;

EID: 0032552058     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(98)00611-5     Document Type: Article

References (33)

1. 1. Salaun, J. ; Baird, M. S. Curr. Med. Chem. 1995, 2, 511-452.
2. 2. Johnson, A. R.; Pearson, J. A.; Shenstone, F. S. ; Fogerty, A. C. Nature 1967, 214, 1244-1245.
3. 3. Johnson, A. R.; Fogerty, A. C.; Pearson, J. A.; Shenstone, F. S. ; Bersten, A. M. Lipids 1968, 4, 265-269.
4. 4. Fogerty, A. C.; Johnson, A. R. ; Pearson, J. A. Lipids 1972, 7, 335-338.
5. 5. Clark, J. R. ; Kircher, H. W. Lipids 1972, 7, 769-772.
6. 6. Raju, P. K. ; Reiser, R. J. Biol. Chem. 1967, 242, 379-384.
7. 7. Allen, E.; Johnson, A. R.; Fogerty, A. C.; Pearson, J. A. ; Shenstone, F. S. Lipids 1967, 2, 419-423.
8. 8. Jeffcoat, R. ; Pollard, M. R. Lipids 1977, 12, 480-485.
9. 9. Ory, R. L. ; Altschul, A. M. Biochem. Biophys. Res. Commun. 1964, 17, 12-16.
10. 10. Pande, S. V. ; Mead, J. F. J. Biol. Chem. 1970, 245, 1856-1861.
11. 11. Arsequell, G.; Fabrias, G. ; Camps, F. Insect Biochem. 1989, 19, 623-627.
12. 12. Gosalbo, L.; Fabrias, G.; Arsequell, G. ; Camps, F. Insect Biochem. and Molec. Biol. 1992, 22, 687-690.
13. 13. Gosalbo, L.; Fabrias, G. ; Camps, F. Arch. Insect Biochem. Physiol. 1994, 26, 279-286.
14. 14. Fabrias, G.; Gosalbo, L.; Quintana, J. ; Camps, F. J. Lipid Res. 1996, 37, 1503-1509.
15. 15. Fabrias, G.; Barrot, M. ; Camps, F. Insect Biochem Molec Biol 1995, 25, 655-660.
16. 16. Ando, T.; Ikemoto, K.; Ohno, R. ; Yamamoto, M. Arch. Insect Biochem. Physiol. 1998, 37, 8-16.
17. 17. Ando, T.; Ohno, R.; Ikemoto, K. ; Yamamoto, M. J. Agric. Food Chem. 1996, 44, 3350-3354.
18. 11 desaturation of palmitic acid. Thus, following the standard bioasssay (see ref. 12) relative amounts of perdeuterated methyl (Z)-11-hexadecenoate formed from perdeuterated palmitic acid in methanolyzed sex pheromone glands were similar in insects treated with either 3 (mean±S.E =16.0±2.5; n=5) or 4 (13.3±1.4; n=10) and in control animals (14.3±1.4; n=10)
19. 19. Norden, W.; Sander, V. ; Weyerstahl, P. Chem. Ber. 1983, 116, 3097-.
20. 20. Gritsenko, E. I.; Plemenkov, V. V.; Butenko, G. G. ; Bolesov, I. G. J. Org. Chem. USSR 1985, 21, 416-417.
21. 21. Gritsenko, E. I.; Butenko, G. G.; Plemenkov, V. V. ; Bolesov, I. G. Dokl. Akad. Nauk. SSSR Ser. Khim. 1986, 289, 99-103.
22. 22. Gritsenko, E. I.; Butenko, G. G.; Plemenkov, V. V. ; Bolesov, I. G. Zh. Obshch. Khim. 1986, 56, 904-909.
23. 23. Shapiro, E. A.; Protopopova, M. N. ; Nefedov, O. M. Bull. Acad. Sci. USSR, Div. Chem. Sci. 1991, 202-204.
24. 24. Kircher, H. W. J. Amer. Oil Chem. Soc. 1964, 41, 4-8.
25. 9 stearoyl ACP desaturase, as determined by X-ray crystallography, the fatty acyl substrate is included into a deep hydrophobic channel extending from the surface into the interior of the enzyme (Lindqvist, Y.; Huang, W.; Schneider, G.; Shanklin, J. The EMBO J. 1996, 15, 4081-4092)
26. 26. Arsequell, G.; Fabrias, G.; Gosalbo, L. ; Camps, F. Chem. Phys. Lipids 1992, 63, 149-158.
27. 27. Williams, J. L. ; Sgoutas, D. S. J. Org. Chem. 1971, 36, 3064-3065.
28. 28. Kartashov, V. R.; Skorobogatova, E. V., Akimkina, N. F. ; Zefirov, N. S. Zh. Org. Khim. 1982, 18, 38-42.
29. 29. Friedrich, E. C. Solvolysis of cyclopropyl-substituted derivatives. In The Chemistry of the Cyclopropyl Group, Rappoport, Z. Ed.; John Wiley and Sons: New York, 1987; pp. 633-700.
30. 30. Isaka, M.; Ejiri, S. ; Nakamura, E. Tetrahedron 1992, 48, 2045-2057.
31. 31. Although it has been reported that cyclopropenones react with dithiols at 20°C in the presence of trifluoroacetic acid to give the bicyclic dithioacetals (Yoshida, H.; Kinoshita, H.; Kato, T.; Kanehira, N.; Ogata, T.; Matsumoto, K. Synthesis 1987, 393-394) no acetalization took place with 1-propanethiol under our conditions.
32. 32. Halton, B. ; Banwell, M. G. Cyclopropenes. In The Chemistry of the Cyclopropyl Group, Rappoport, Z. Ed.; John Wiley and Sons: New York, 1987; pp. 1300-1301.
33. 33. It has been reported that diphenylcyclopropenone reacts with alkylamines in ethanol under reflux to give the corresponding α,β-diphenylacrylamide derivatives (Eicher, T.; Boehm, S.; Ehrhardt, H.; Harth, R.; Lerch, D. Liebigs Ann. Chem. 1981, 765-771). However, this reaction cannot be considered biologically relevant due to the harsh conditions used.