Critical role of the linking amide in CC-1065 and the duocarmycins: Implications on the source of DNA alkylation catalysis

Journal of the American Chemical Society

Volumn 120, Issue 45, 1998, Pages 11554-11557

  Boger, Dale L ^a   Santillán Jr , Alejandro ^a   Searcey, Mark ^a   Jin, Qing ^a  

^a SCRIPPS RESEARCH INSTITUTE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ANTINEOPLASTIC ANTIBIOTIC; DUOCARMYCIN; RACHELMYCIN; UNCLASSIFIED DRUG;

ALKYLATION; ANTINEOPLASTIC ACTIVITY; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CATALYSIS; CHEMICAL STRUCTURE; CYTOTOXICITY; DRUG DNA BINDING; DRUG SYNTHESIS; ENANTIOMER; HALF LIFE TIME; PROTON NUCLEAR MAGNETIC RESONANCE;

EID: 0032545027     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja9818093     Document Type: Article

References (8)

1. Boger, D. L.; Boyce, C. W.; Garbaccio, R. M.; Goldberg, J. Chem. Rev. 1997, 97, 787. Boger, D. L.; Johnson, D. S. Angew. Chem., Int. Ed. Engl. 1996, 35, 1439. Boger, D. L.; Johnson, D. S. Proc. Natl. Acad. Sci. U.S.A. 1995, 92, 3642. Boger, D. L. Acc. Chem. Res. 1995, 28, 20. Boger, D. L. Chemtracts: Org. Chem. 1991, 4, 329. Boger, D. L. Proc. Robert A. Welch Found. Conf. Chem. Res., XXXV. Chem. From. Med. 1991, 35, 137. Boger, D. L. In Advances in Heterocyclic Natural Products Synthesis; Pearson, W. H., Ed.; JAI: Greenwich, CT, 1992; Vol. 2, p 1. Boger, D. L.; Coleman, R. S. In Studies in Natural Products Chemistry; Atta-ur-Rahman, Ed.; Elsevier: Amsterdam, 1989; Vol. 3, p 301.
2. Boger, D. L.; Boyce, C. W.; Garbaccio, R. M.; Goldberg, J. Chem. Rev. 1997, 97, 787. Boger, D. L.; Johnson, D. S. Angew. Chem., Int. Ed. Engl. 1996, 35, 1439. Boger, D. L.; Johnson, D. S. Proc. Natl. Acad. Sci. U.S.A. 1995, 92, 3642. Boger, D. L. Acc. Chem. Res. 1995, 28, 20. Boger, D. L. Chemtracts: Org. Chem. 1991, 4, 329. Boger, D. L. Proc. Robert A. Welch Found. Conf. Chem. Res., XXXV. Chem. From. Med. 1991, 35, 137. Boger, D. L. In Advances in Heterocyclic Natural Products Synthesis; Pearson, W. H., Ed.; JAI: Greenwich, CT, 1992; Vol. 2, p 1. Boger, D. L.; Coleman, R. S. In Studies in Natural Products Chemistry; Atta-ur-Rahman, Ed.; Elsevier: Amsterdam, 1989; Vol. 3, p 301.
3. Boger, D. L.; Boyce, C. W.; Garbaccio, R. M.; Goldberg, J. Chem. Rev. 1997, 97, 787. Boger, D. L.; Johnson, D. S. Angew. Chem., Int. Ed. Engl. 1996, 35, 1439. Boger, D. L.; Johnson, D. S. Proc. Natl. Acad. Sci. U.S.A. 1995, 92, 3642. Boger, D. L. Acc. Chem. Res. 1995, 28, 20. Boger, D. L. Chemtracts: Org. Chem. 1991, 4, 329. Boger, D. L. Proc. Robert A. Welch Found. Conf. Chem. Res., XXXV. Chem. From. Med. 1991, 35, 137. Boger, D. L. In Advances in Heterocyclic Natural Products Synthesis; Pearson, W. H., Ed.; JAI: Greenwich, CT, 1992; Vol. 2, p 1. Boger, D. L.; Coleman, R. S. In Studies in Natural Products Chemistry; Atta-ur-Rahman, Ed.; Elsevier: Amsterdam, 1989; Vol. 3, p 301.
4. Boger, D. L.; Boyce, C. W.; Garbaccio, R. M.; Goldberg, J. Chem. Rev. 1997, 97, 787. Boger, D. L.; Johnson, D. S. Angew. Chem., Int. Ed. Engl. 1996, 35, 1439. Boger, D. L.; Johnson, D. S. Proc. Natl. Acad. Sci. U.S.A. 1995, 92, 3642. Boger, D. L. Acc. Chem. Res. 1995, 28, 20. Boger, D. L. Chemtracts: Org. Chem. 1991, 4, 329. Boger, D. L. Proc. Robert A. Welch Found. Conf. Chem. Res., XXXV. Chem. From. Med. 1991, 35, 137. Boger, D. L. In Advances in Heterocyclic Natural Products Synthesis; Pearson, W. H., Ed.; JAI: Greenwich, CT, 1992; Vol. 2, p 1. Boger, D. L.; Coleman, R. S. In Studies in Natural Products Chemistry; Atta-ur-Rahman, Ed.; Elsevier: Amsterdam, 1989; Vol. 3, p 301.
5. Boger, D. L.; Boyce, C. W.; Garbaccio, R. M.; Goldberg, J. Chem. Rev. 1997, 97, 787. Boger, D. L.; Johnson, D. S. Angew. Chem., Int. Ed. Engl. 1996, 35, 1439. Boger, D. L.; Johnson, D. S. Proc. Natl. Acad. Sci. U.S.A. 1995, 92, 3642. Boger, D. L. Acc. Chem. Res. 1995, 28, 20. Boger, D. L. Chemtracts: Org. Chem. 1991, 4, 329. Boger, D. L. Proc. Robert A. Welch Found. Conf. Chem. Res., XXXV. Chem. From. Med. 1991, 35, 137. Boger, D. L. In Advances in Heterocyclic Natural Products Synthesis; Pearson, W. H., Ed.; JAI: Greenwich, CT, 1992; Vol. 2, p 1. Boger, D. L.; Coleman, R. S. In Studies in Natural Products Chemistry; Atta-ur-Rahman, Ed.; Elsevier: Amsterdam, 1989; Vol. 3, p 301.
6. Boger, D. L.; Boyce, C. W.; Garbaccio, R. M.; Goldberg, J. Chem. Rev. 1997, 97, 787. Boger, D. L.; Johnson, D. S. Angew. Chem., Int. Ed. Engl. 1996, 35, 1439. Boger, D. L.; Johnson, D. S. Proc. Natl. Acad. Sci. U.S.A. 1995, 92, 3642. Boger, D. L. Acc. Chem. Res. 1995, 28, 20. Boger, D. L. Chemtracts: Org. Chem. 1991, 4, 329. Boger, D. L. Proc. Robert A. Welch Found. Conf. Chem. Res., XXXV. Chem. From. Med. 1991, 35, 137. Boger, D. L. In Advances in Heterocyclic Natural Products Synthesis; Pearson, W. H., Ed.; JAI: Greenwich, CT, 1992; Vol. 2, p 1. Boger, D. L.; Coleman, R. S. In Studies in Natural Products Chemistry; Atta-ur-Rahman, Ed.; Elsevier: Amsterdam, 1989; Vol. 3, p 301.
7. Boger, D. L.; Boyce, C. W.; Garbaccio, R. M.; Goldberg, J. Chem. Rev. 1997, 97, 787. Boger, D. L.; Johnson, D. S. Angew. Chem., Int. Ed. Engl. 1996, 35, 1439. Boger, D. L.; Johnson, D. S. Proc. Natl. Acad. Sci. U.S.A. 1995, 92, 3642. Boger, D. L. Acc. Chem. Res. 1995, 28, 20. Boger, D. L. Chemtracts: Org. Chem. 1991, 4, 329. Boger, D. L. Proc. Robert A. Welch Found. Conf. Chem. Res., XXXV. Chem. From. Med. 1991, 35, 137. Boger, D. L. In Advances in Heterocyclic Natural Products Synthesis; Pearson, W. H., Ed.; JAI: Greenwich, CT, 1992; Vol. 2, p 1. Boger, D. L.; Coleman, R. S. In Studies in Natural Products Chemistry; Atta-ur-Rahman, Ed.; Elsevier: Amsterdam, 1989; Vol. 3, p 301.
8. Boger, D. L.; Boyce, C. W.; Garbaccio, R. M.; Goldberg, J. Chem. Rev. 1997, 97, 787. Boger, D. L.; Johnson, D. S. Angew. Chem., Int. Ed. Engl. 1996, 35, 1439. Boger, D. L.; Johnson, D. S. Proc. Natl. Acad. Sci. U.S.A. 1995, 92, 3642. Boger, D. L. Acc. Chem. Res. 1995, 28, 20. Boger, D. L. Chemtracts: Org. Chem. 1991, 4, 329. Boger, D. L. Proc. Robert A. Welch Found. Conf. Chem. Res., XXXV. Chem. From. Med. 1991, 35, 137. Boger, D. L. In Advances in Heterocyclic Natural Products Synthesis; Pearson, W. H., Ed.; JAI: Greenwich, CT, 1992; Vol. 2, p 1. Boger, D. L.; Coleman, R. S. In Studies in Natural Products Chemistry; Atta-ur-Rahman, Ed.; Elsevier: Amsterdam, 1989; Vol. 3, p 301.