Cryptoregiochemistry of the Δ11-myristoyl-CoA desaturase involved in the biosynthesis of Spodoptera littoralis sex pheromone

Biochemistry

Volumn 38, Issue 46, 1999, Pages 15272-15277

  Pinilla, Anna ^a   Camps, Francisco ^a   Fabrias, Gemma ^a  

^a DEPARTMENT OF ENVIRONMENTAL CHEMISTRY   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

COENZYME A; DECANOIC ACID DERIVATIVE; SEX PHEROMONE; UNSATURATED FATTY ACID; ACYL COENZYME A DESATURASE; DELTA 13 FATTY ACID DESATURASE; DELTA-13 FATTY ACID DESATURASE; DELTA11 MYRISTOYL COENZYME A DESATURASE; DELTA11-MYRISTOYL-COENZYME A DESATURASE; DEUTERIUM; MYRISTIC ACID;

ARTICLE; ENZYME ACTIVE SITE; ENZYME ANALYSIS; ENZYME CONFORMATION; ENZYME REGULATION; ENZYME SUBSTRATE; FATTY ACID DESATURATION; HORMONE SYNTHESIS; HYDROGEN BOND; LEPIDOPTERA; PRIORITY JOURNAL; ANIMAL; ARMYWORM; BIOSYNTHESIS; CHEMISTRY; CONFORMATION; ENZYMOLOGY; FEMALE; MASS FRAGMENTOGRAPHY; METABOLISM; STEREOISOMERISM;

ANIMALS; DEUTERIUM; FATTY ACID DESATURASES; FEMALE; GAS CHROMATOGRAPHY-MASS SPECTROMETRY; MOLECULAR CONFORMATION; MYRISTIC ACID; SEX ATTRACTANTS; SPODOPTERA; STEREOISOMERISM;

EID: 0033576218     PISSN: 00062960     EISSN: None     Source Type: Journal    
DOI: 10.1021/bi990972n     Document Type: Article

References (38)

1. Cook, H. (1985) in Biochemistry of Lipids and Membranes (Vance, D. E., and Vance, J. E., Eds.) pp 189-203, The Benjamin Cummings Publishing Co. Ltd., Menlo Park, CA.
2. Shanklin, J., and Cahoon, E. B. (1998) Annu. Rev. Plant Physiol. Mol. Biol. 49, 611-641.
3. Roelofs, W. L., and Bjostad, L. (1984) Bioorg. Chem. 12, 279-298.
4. Bjostad, L. B., and Roelofs, W. L. (1981) J. Biol. Chem. 256, 7936-7940.
5. Bjostad, L. D., and Roelofs, W. L. (1983) Science 220, 1387-1389.
6. Martinez, T., Fabrias, G., and Camps, F. (1990) J. Biol. Chem. 265, 1381-1387.
7. Jurenka, R. A., Jacquin, E., and Roelofs, W. L. (1991) Arch. Insect Biochem. Phsyiol 17, 81-91.
8. Wolf, W. A., and Roelofs, W. L. (1986) Arch. Insect. Biochem. Physiol. 3, 45-52.
9. Rodriguez, F., Hallahan, D. L., Pickett, J. A., and Camps, F. (1992) Insect Biochem. Mol. Biol. 22, 143-148.
10. Lofstedt, C., and Bengtsson, M. (1988) J. Chem. Ecol. 14, 903-914.
11. Foster, S. P., and Roelofs, W. L. (1990) Experientia 46, 269-273.
12. Zhao, C., Lofstedt, C., and Wang, X. (1990) Arch. Insect Biochem. Physiol. 15, 57-65.
13. Buist, P. H., and Marecak, D. M. (1992) J. Am. Chem. Soc. 114, 5073-5080.
14. Collins, J. R., Camper, D. L., and Loew, G. H. (1991) J. Am. Chem. Soc. 113, 2736-2743.
15. Akhtar, M., and Wright, J. N. (1991) Nat. Prod. Rep. 8, 527-551.
16. Buist, P. H., and Behrouzian, B. (1996) J. Am. Chem. Soc. 118, 6295-6296.
17. Buist, P. H., and Behrouzian, B. (1998) J. Am. Chem. Soc. 120, 871-876.
18. Navarro, I., Font, I., Fabrias, G., and Camps, F. (1997) J. Am. Chem. Soc. 119, 11335-11336.
19. Boland, W., Frossl, C., Schottler, M., and Toth, M. (1993) J. Chem. Soc., Chem. Commun. 1155-1157.
20. Schroepfer, G. J., and Bloch, K. (1965) J. Biol. Chem. 240, 54-63.
21. Morris, L. J. (1964) Biochem. Biophys. Res. Commun. 29, 311-315.
22. Morris, L. J., Harris, R. V., Kelly, W., and James, A. T. (1968) Biochem. J. 109, 673-678.
23. Dunkelblum, E., and Kehat, M. (1987) Insect Biochem. 17, 877-881.
24. The use of thiafatty acids as alternative substrates for desaturases has been reported; see refs 16 and 17.
25. Seebach, D., Jones, N. R., and Corey, E. J. (1968) J. Org. Chem. 33, 300-305.
26. Seebach, D. (1969) Angew. Chem., Int. Ed. Engl. 8, 639-649.
27. Cain, E. N., and Welling, L. L. (1975) Tetrahedron Lett., 1353-1356.
28. Wai-si, E., Prestwich, D. (1988) J. Lab. Comput. Radiopharm. 25, 627-633.
29. Wirberg, K. B., and Pfeiffer, G. J. (1970) J. Am. Chem. Soc. 92, 553-564.
30. Brown, H. C., and Krishnamurthy, S. (1980) J. Org. Chem. 54, 849-856.
31. Auerbach, J., and Weinreb, S. M. (1974) J. Chem. Soc., Chem. Commun. 298-299.
32. Goerger, M. M., and Hudson, B. S. (1988) J. Org. Chem. 53, 3148-3153.
33. Rettie, A. E., Boberg, M., Rettenmeier, A. W., and Baillie, T. A. (1988) J. Biol. Chem. 263, 13733-13738.
34. Baenziger, J. E., Smith, I. C. P., and Hill, R. J. (1990) Chem. Phys. Lipids 54, 17-23.
35. Gosalbo, L., Fabrias, G., Arsequell, G., and Camps, F. (1992) Insect Biochem. Mol. Biol. 22, 687-690.
36. Valentine, A. M., Wilkinson, B., Liu, K. E., Komar-Panicucci, S., Priestley, N. D., Morimoto, H., Floss, H. G., and Lippard, S. J. (1997) J. Am. Chem. Soc. 119, 1818-1827.
37. Cahoon, E. B., Lindqvist, Y., Schneider, G., Shanklin, J. (1997) Proc. Natl. Acad. Sci. U.S.A. 94, 4872-4877.
38. Knipple, D. C., Rosenfield, C. L., Miller, S. J., Liu, W., Tang, J., Ma, P. W., and Roelofs, W. L. (1998) Proc. Natl. Acad. Sci. U.S.A. 95, 15287-15292.