Solution kinetics of CC-1065 A-ring opening: Substituent effects and general acid/base catalysis

Journal of the American Chemical Society

Volumn 128, Issue 11, 2006, Pages 3722-3727

  LaBarbera, Daniel V ^a   Skibo, Edward B ^a  

^a ARIZONA STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYLATION; CARBONYLATION; CARRIER CONCENTRATION; CATALYSIS; DNA; NITROGEN; OXYGEN;

CYCLOPROPYL GROUP; CYCLOPROPYL RING; NUCLEOPHILE TRAPPING; SOLUTION KINETICS;

DERIVATIVES;

CYCLOPROPANE DERIVATIVE; DNA;

ACID BASE BALANCE; ALKYLATION; ARTICLE; CALCULATION; CATALYSIS; ELECTRON TRANSPORT; KINETICS; PH MEASUREMENT; REACTION ANALYSIS; RING OPENING;

ANTIBIOTICS, ANTINEOPLASTIC; CATALYSIS; HYDROGEN-ION CONCENTRATION; INDOLES; KINETICS; MODELS, MOLECULAR; SOLUTIONS;

EID: 33645406939     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja057289a     Document Type: Article

References (21)

1. Boger, D. L.; Johnson, D. S. Angew. Chem., Int. Ed. Engl. 1996, 35, 1438-1474.
2. Cacciari, B.; Romagnoli, R.; Baraldi, P. G.; DaRos, T.; Spalluto, G. Expert Opin. Ther. Patents 2000, 10, 1853-1871.
3. Searcey, M. Curr. Pharm. Des. 2002, 1375-1389.
4. Lin, C. H.; Beale, J. M.; Hurley, L. H. Biochemistry 1991, 30, 3597-3602.
5. Eis, P. S.; Smith, J. A.; Rydzewski, J. M.; Case, D. A.; Boger, D. L.; Chazin, W. J. J. Mol. Biol. 1997, 272, 237-252.
6. Warpehoski, M. A.; Harper, D. E. J. Am. Chem. Soc. 1994, 116, 7573-80.
7. Boger, D. L.; Garbaccio, R. M. J. Org. Chem. 1999, 64, 8350-8362.
8. Boger, D. L.; Garbaccio, R. M. Acct. Chem. Res. 1999, 32, 1043-1052.
9. Boger, D. L.; Boyce, C. W.; Johnson, D. S. Bioorg. Med. Chem. Lett. 1997, 7, 233-238.
10. Skibo, E. B.; Xing, C. Biochemistry 1998, 37, 15199-15213.
11. Beecham, L. M.; Brand, L. Photochem. Photobiol. 1986, 44, 323-329.
12. Matheson, I. B. C. Anal. Instrum. 1987, 16, 345-373.
13. Warpehoski, M. A.; Gebhard, I.; Kelly, R. C.; Krueger, W. C.; Li, L. H.; McGovren, J. P.; Prairie, M. D.; Wienienski, N.; Wierenga, W. J. Med. Chem. 1988, 31, 590-603,
14. Durig, J. R.; Berry, R. J.; Durig, D. T.; Sullivan, J. F.; Little, T. S. Teubner-Texte Phys. 1988, 20, 54-68.
15. Fersht, A. Enzyme Structure and Mechanism; W. H. Freeman: San Francisco, CA, 1977; pp 84-89.
16. Boger, D. L.; Ishizaki, T.; Kitos, P. A.; Suntornwat, O. J. Org. Chem. 1990, 55, 5823-32.
17. Boger, D. L.; McKie, J. A.; Nishi, T.; Ogiku, T. J. Am. Chem. Soc. 1997, 119, 311-325.
18. Boger, D. L.; McKie, J. A.; Han, N.; Tarby, C. M.; Riggs, H. W.; Kitos, P. A. Bioorg. Med. Chem. Lett. 1996, 6, 659-64.
19. Boger, D. L.; Garbaccio, R. M. J. Org. Chem. 1999, 64, 5666-5669.
20. Park, H.-J. Arch. Pharm. Res. 2002, 25, 11-24.
21. Warpehoski, M. A.; Harper, D. E. J. Am. Chem. Soc. 1995, 117, 2951-2952.