Biosynthesis of squalene. Evidence for a tertiary cyclopropylcarbinyl cationic intermediate in the rearrangement of presqualene diphosphate to squalene

Journal of the American Chemical Society

Volumn 118, Issue 51, 1996, Pages 13089-13090

  Jarstfer, Michael B ^a   Blagg, Brian S J ^a   Rogers, Daniel H ^a   Poulter, C Dale ^a  

^a UNIVERSITY OF UTAH   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

SQUALENE; SQUALENE SYNTHASE;

ARTICLE; BIOSYNTHESIS; ENZYME ACTIVITY; REACTION ANALYSIS; YEAST;

EID: 0030452754     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja963308s     Document Type: Article

References (21)

1. i, inorganic pyrophosphate; PSOH, presqualene alcohol; PSPP, presqualene diphosphate; RIOH, rillingol; SQ, squalene; SQSase, squalene synthase.
2. Poulter, C. D.; Marsh, L. L.; Hughes, J. M.; Argyle, J. C.; Satterwhite, D. M.; Goodfellow, R. J.; Moesinger, S. G. J. Am. Chem. Soc. 1977, 99, 3816-3823.
3. Poulter, C. D.; Rilling, H. C. Biosynthesis of Isoprenoid Compounds; Porter, J. W., Spurgeon, S. L., Eds; Wiley: New York, 1981; Vol. 1, pp 413-441.
4. Poulter, C. D. Acc. Chem. Res. 1990, 23, 70-77.
5. van Tamelen, E. E.; Schwartz, M. A. J. Am. Chem. Soc. 1971, 93, 1780-1782.
6. Altman, L. J.; Kowerski, R. C.; Rilling, H. C. J. Am. Chem. Soc. 1971, 93, 1782-1783.
7. Rilling, H. C.; Poulter, C. D.; Epstein, W. W. Larsen, B. J. Am. Chem. Soc. 1971, 93, 1783-1785.
8. Coates, R. M.; Robinson, W. H. J. Am. Chem. Soc. 1972, 94, 5920-5921.
9. Zhang, D.; Poulter, C. D. J. Am. Chem. Soc. 1995, 117, 1641-1642.
10. Zhang, D.; Jennings, S. M.; Robinson, G. W.; Poulter, C. D. Arch. Biochem. Biophys. 1993, 304, 133-143.
11. The product distribution is slightly different than originally reported because of improved HPLC conditions. We were able to detect several minor components that accounted for ca. 4% of the total.
12. Huang, Z.; Poulter, C. D. J. Am. Chem. Soc. 1989, 111, 2713-2715.
13. Rilling, H. C. J. Biol. Chem. 1966, 241, 3233-3236.
14. Dave, K. G.; Dunlap. R. B.; Jain, M. K.; Cordes, E. H.; Wenkert, E. J. Biol. Chem. 1968, 243, 1073-1074.
15. 1) + [NADPH]).
16. Products were chromatographed on a Microsorb-MV 5 μm silica gel column with isocratic elution using 1:20 (v/v) tert-butyl methyl ether/ hexane.
17. 50O: calcd 426.3861, found 426.3865.
18. Ortiz de Montellano, P. R.; Corey, E. J. Tetrahedron Lett. 1968, 5113-5115.
19. Poulter, C. D.; Mosinger, S. G.; Epstein, W. W. Tetrahedron Lett. 1972, 67-70.
20. Poulter, C. D.; Muscio, O. J.; Goodfellow, R. J. Biochemistry 1974, 13, 1530-1538.
21. Charette, A. B.; Juteau, H. J. Am. Chem. Soc. 1994, 116, 2651-2652.