Vibrational circular dichroism analysis reveals a conformational change of the baccatin III ring of paclitaxel: Visualization of conformations using a new code for structure-activity relationships

Journal of Organic Chemistry

Volumn 73, Issue 6, 2008, Pages 2367-2372

  Izumi, Hiroshi ^a   Ogata, Atsushi ^a   Nafie, Laurence A ^b,c   Dukor, Rina K ^c  

^a NATIONAL INSTITUTE OF ADVANCED INDUSTRIAL SCIENCE AND TECHNOLOGY AIST   (Japan)

^b SYRACUSE UNIVERSITY   (United States)

^c BIOTOOLS INC   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

COMPUTATIONAL COMPLEXITY; CRYSTAL STRUCTURE; DICHROISM; MOLECULAR INTERACTIONS;

COMPUTATIONAL ANALYSES; ELECTRON MICROGRAPH;

MOLECULAR VIBRATIONS;

BACCATIN III; BETA TUBULIN; CARBONYL DERIVATIVE; HYDROXYL GROUP; PACLITAXEL; TUBULIN;

ARTICLE; CIRCULAR DICHROISM; CONFORMATIONAL TRANSITION; CRYSTAL STRUCTURE; GENOME ANALYSIS; PROTEIN BINDING; STRUCTURE ACTIVITY RELATION;

ALKALOIDS; ANTINEOPLASTIC AGENTS, PHYTOGENIC; CIRCULAR DICHROISM; MODELS, MOLECULAR; MOLECULAR CONFORMATION; MOLECULAR STRUCTURE; PACLITAXEL; STRUCTURE-ACTIVITY RELATIONSHIP; TAXOIDS;

EID: 41849102050     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo7026382     Document Type: Article

References (22)

1. (a) Alcaraz, A. A.; Mehta, A. K.; Johnson, S. A.; Snyder, J. P. J. Med. Chem. 2006, 49, 2478-2488.
2. (b) Tang, S.; Yang, C.; Brodie, P.; Bane, S.; Ravindra, R.; Sharma, S.; Jiang, Y.; Snyder, J. P.; Kingston, D. G. I. Org. Lett. 2006, 8, 3983-3986.
3. (c) Sánchez-Pedregal, V. M.; Kubicek, K.; Meiler, J.; Lyothier, I.; Paterson, I.; Carlomagno, T. Angew. Chem., Int. Ed. 2006, 45, 7388-7394.
4. (d) Johnson, S. A.; Alcaraz, A. A.; Snyder, J. P. Org. Lett. 2005, 7, 5549-5552.
5. (a) Gautier, C.; B Bürgi, T. J. Am. Chem. Soc. 2006, 128, 11079-11087.
6. (b) Kuppens, T.; Herrebout, W.; van der Veken, B.; Bultinck, P. J. Phys. Chem. A 2006, 110, 10191-10200.
7. (c) Naubron, J.-V.; Giordano, L.; Fotiadu, F.; Bürgi, T.; Vanthuyne, N.; Roussel, C.; Buono, G. J. Org. Chem. 2006, 71, 5586-5593.
8. (d) Monde, K.; Miura, N.; Hashimoto, M.; Taniguchi, T.; Inabe, T. J. Am. Chem. Soc. 2006, 128, 6000-6001.
9. (e) Brotin, T.; Cavagnat, D.; Dutasta, J.-P.; Buffeteau, T. J. Am. Chem. Soc. 2006, 128, 5533-5540.
10. (f) Vargas, A.; Bonalumi, N.; Ferri, D.; Baiker, A. J. Phys. Chem. A 2006, 110, 1118-1127.
11. (g) Furo, T.; Mori, T.; Wada, T.; Inoue, Y. J. Am. Chem. Soc. 2005, 127, 8242-8243.
12. (h) Izumi, H.; Futamura, S.; Nafie, L. A.; Dukor, R. K. Chem. Rec. 2003, 3, 112-119.
13. (i) Freedman, T. B.; Cao, X. L.; Dukor, R. K.; Nafie, L. A. Chirality 2003, 15, 743-758.
14. (j) Wang, F.; Wang, Y.; Polavarapu, P. L.; Li, T.; Drabowicz, J.; Pietrusiewicz, K. M.; Zygo, K. J. Org. Chem. 2002, 67, 6539-6541.
15. (k) Cheeseman, J. R.; Frisch, M. J.; Devlin, F. J.; Stephens, P. J. Chem. Phys. Lett. 1996, 252, 211-220.
16. Izumi, H.; Yamagami, S.; Futamura, S.; Nafie, L. A.; Dukor, R. K. J. Am. Chem. Soc. 2004, 126, 194-198.
17. Izumi, H.; Futamura, S.; Tokita, N.; Hamada, Y. J. Org. Chem. 2007, 72, 277-279.
18. (a) Cross, L. C.; Klyne, W. Pure Appl. Chem. 1976, 45, 11-30.
19. (b) International Union of Pure and Applied Chemistry, Organic Chemistry Division, Commission on Nomenclature of Organic Chemistry. In Nomenclature of Organic Chemistry, Sections A, B, C, D, E, F, and H; Rigaudy, J., Klesney, S., Eds.; Pergamon Press: Oxford, UK, 1979.
20. Löwe, J.; Li, H.; Downing, K. H.; Nogales, E. J. Mol. Biol. 2001, 313, 1045-1057.
21. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Montgomery, J. A., Jr.; Vreven, T.; Kudin, K. N.; Burant, J. C.; Millam, J. M.; Iyengar, S. S.; Tomasi, J.; Barone, V.; Mennucci, B.; Cossi, M.; Scalmani, G.; Rega, N.; Petersson, G. A.; Nakatsuji, H.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Klene, M.; Li, X.; Knox, J. E.; Hratchian, H. P.; Cross, J. B.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Ayala, P. Y.; Morokuma, K.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Zakrzewski, V. G.; Dapprich, S.; Daniels, A. D.; Strain, M. C.; Farkas, O.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Ortiz, J. V.; Cui, Q.; Baboul, A. G.; Clifford, S.; Cioslowski, J.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Challacombe, M.; Gill, P. M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Gonzalez, C.; Pople, J. A. Gaussian 03, Revision B.04; Gaussian, Inc.: Pittsburgh, PA, 2003.
22. See the Supporting Information.