Formation of ring A in the biosynthesis of hopanoids from squalene. A density functional study

Collection of Czechoslovak Chemical Communications

Volumn 69, Issue 1, 2004, Pages 261-266

  Hess Jr , B Andes ^a  

^a VANDERBILT UNIVERSITY   (United States)

Author keywords

Ab initio calculations; Biosynthesis; Cyclizations; DTF calculations; Reaction mechanism; Squalene; Steroids; Triterpenes

Indexed keywords

CATION; HOPANOID; METHYL GROUP; SQUALENE; TRITERPENE;

ARTICLE; BIOSYNTHESIS; CHEMICAL ANALYSIS; CHEMICAL STRUCTURE; CONFORMATION; DENSITOMETRY; MATHEMATICAL ANALYSIS;

EID: 1642330712     PISSN: 00100765     EISSN: None     Source Type: Journal    
DOI: 10.1135/cccc20040261     Document Type: Article

References (14)

1. See reviews: a) Abe L., Rohmer M., Restwich G. D.: Chem. Rev. 1993, 93, 2189; b) Wendt K. U., Schulz G. E., Corey E. J., Liu D. R.: Angew. Chem., Int. Ed. 2000, 39, 2812; c) Kannenberg E. L., Poralla K.: Naturwissenschaften 1999, 86, 168.
2. See reviews: a) Abe L., Rohmer M., Restwich G. D.: Chem. Rev. 1993, 93, 2189; b) Wendt K. U., Schulz G. E., Corey E. J., Liu D. R.: Angew. Chem., Int. Ed. 2000, 39, 2812; c) Kannenberg E. L., Poralla K.: Naturwissenschaften 1999, 86, 168.
3. See reviews: a) Abe L., Rohmer M., Restwich G. D.: Chem. Rev. 1993, 93, 2189; b) Wendt K. U., Schulz G. E., Corey E. J., Liu D. R.: Angew. Chem., Int. Ed. 2000, 39, 2812; c) Kannenberg E. L., Poralla K.: Naturwissenschaften 1999, 86, 168.
4. a) Gao D., Pan Y.-K., Byun K., Gao J.: J. Am. Chem. Soc. 1998, 120, 4045;
5. b) Jenson C., Jorgensen W. L.: J. Am. Chem. Soc. 1997, 119, 10846;
6. c) Hess B. A., Jr.: Collect. Czech. Chem. Commun. 2003, 68, 202;
7. d) Hess B. A., Jr.: J. Am. Chem. Soc. 2002, 124, 10286;
8. e) Hess B. A., Jr.: Org. Lett. 2003, 5, 165.
9. Frisch M. J., Trucks G. W., Schlegel H. B., Scuseria G. E., Robb M. A., Cheeseman J. R., Zakrzewski V. G., Montgomery J. A., Jr., Stratmann R. E., Burant J. C., Dapprich S., Millam J. M., Daniels A. D., Kudin K. N., Strain M. C., Farkas O., Tomasi J., Barone V., Cossi M., Cammi R., Mennucci B., Pomelli C., Adamo C., Clifford S., Ochterski J., Petersson G. A., Ayala P. Y., Cui Q., Morokuma K., Malick D. K., Rabuck A. D., Raghavachari K., Foresman J. B., Cioslowski J., Ortiz J. V., Stefanov B. B., Liu G., Liashenko A., Piskorz P., Komaromi I., Gomperts R., Martin R. L., Fox D. J., Keith T., Al-Laham M. A., Peng C. Y., Nanayakkara A., Gonzalez C., Challacombe M., Gill P. M. W., Johnson B., Chen W., Wong M. W., Andres J. L., Gonzalez C., Head-Gordon M., Replogle E. S., Pople J. A.: Gaussian 98W. Gaussian Inc., Pittsburgh (PA) 1998.
10. Becke A. D.: J. Chem. Phys. 1993, 98, 5648.
11. Lee C., Yang W., Parr R. G.: Phys. Rev. B: Condens. Matter 1988, 37, 785.
12. Hariharan P. C., Pople J. A.: Theor. Chim. Acta 1973, 28, 213.
13. a) Gonzalez C., Schlegel H. B.: J. Chem. Phys. 1989, 90, 2154;
14. b) Gonzalez C., Schlegel H. B.: J. Phys. Chem. 1990, 94, 5523.