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Volumn 120, Issue 44, 1998, Pages 11219-11225

Highly selective DNA alkylation at the 5' side G of a 5'GG3' sequence by an aglycon model of pluramycin antibiotics through preferential intercalation into the GG step

Author keywords

[No Author keywords available]

Indexed keywords

ALTROMYCIN B; ANTIBIOTIC AGENT; DNA; GUANINE; KAPURIMYCIN A3; OLIGODEOXYNUCLEOTIDE; PHOSPHORUS 32; PLURAMYCIN; UNCLASSIFIED DRUG;

EID: 0032508975     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja980801q     Document Type: Article
Times cited : (39)

References (29)
  • 17
    • 0031055494 scopus 로고    scopus 로고
    • For recent examples of different DNA alkylation properties of drug enantiomers, see: (a) Boger, D. L.; McKie, J. A.; Nishi, T.; Ogiku, T. J. Am. Chem. Soc. 1997, 119, 311-325. (b) Patel, V. F.; Andis, S. L.; Enkema, J. K.; Johnson, D. A.; Kennedy, J. H.; Mohamadi, F.; Schultz, R. M.; Soose, D. J.; Spees, M. M. J. Org. Chem. 1997, 62, 8868-8874. Borger, D. L.; Yun, W. J. Am. Chem. Soc. 1994, 116, 7996-8006. Boger, D. L.; Johnson, D. S.; Yun, W. J. Am. Chem. Soc. 1994, 116, 1635-1656. (e) Kigoshi, H.; Imamura, Y.; Mizuta, K.; Niwa, H.; Yamada, K. J. Am. Chem. Soc. 1993, 115, 3056-3065. (f) Boger, D. L.; Yun, W.; Terashima, S. Fukuda, Y.; Nakatani, K.; Kitos, P.; Jin, Q. Bioorg. Med. Chem. Lett. 1992, 2, 759-765.
    • (1997) J. Am. Chem. Soc. , vol.119 , pp. 311-325
    • Boger, D.L.1    McKie, J.A.2    Nishi, T.3    Ogiku, T.4
  • 18
    • 0031467660 scopus 로고    scopus 로고
    • For recent examples of different DNA alkylation properties of drug enantiomers, see: (a) Boger, D. L.; McKie, J. A.; Nishi, T.; Ogiku, T. J. Am. Chem. Soc. 1997, 119, 311-325. (b) Patel, V. F.; Andis, S. L.; Enkema, J. K.; Johnson, D. A.; Kennedy, J. H.; Mohamadi, F.; Schultz, R. M.; Soose, D. J.; Spees, M. M. J. Org. Chem. 1997, 62, 8868-8874. Borger, D. L.; Yun, W. J. Am. Chem. Soc. 1994, 116, 7996-8006. Boger, D. L.; Johnson, D. S.; Yun, W. J. Am. Chem. Soc. 1994, 116, 1635-1656. (e) Kigoshi, H.; Imamura, Y.; Mizuta, K.; Niwa, H.; Yamada, K. J. Am. Chem. Soc. 1993, 115, 3056-3065. (f) Boger, D. L.; Yun, W.; Terashima, S. Fukuda, Y.; Nakatani, K.; Kitos, P.; Jin, Q. Bioorg. Med. Chem. Lett. 1992, 2, 759-765.
    • (1997) J. Org. Chem. , vol.62 , pp. 8868-8874
    • Patel, V.F.1    Andis, S.L.2    Enkema, J.K.3    Johnson, D.A.4    Kennedy, J.H.5    Mohamadi, F.6    Schultz, R.M.7    Soose, D.J.8    Spees, M.M.9
  • 19
    • 0028036453 scopus 로고
    • For recent examples of different DNA alkylation properties of drug enantiomers, see: (a) Boger, D. L.; McKie, J. A.; Nishi, T.; Ogiku, T. J. Am. Chem. Soc. 1997, 119, 311-325. (b) Patel, V. F.; Andis, S. L.; Enkema, J. K.; Johnson, D. A.; Kennedy, J. H.; Mohamadi, F.; Schultz, R. M.; Soose, D. J.; Spees, M. M. J. Org. Chem. 1997, 62, 8868-8874. (c) Borger, D. L.; Yun, W. J. Am. Chem. Soc. 1994, 116, 7996-8006. Boger, D. L.; Johnson, D. S.; Yun, W. J. Am. Chem. Soc. 1994, 116, 1635-1656. (e) Kigoshi, H.; Imamura, Y.; Mizuta, K.; Niwa, H.; Yamada, K. J. Am. Chem. Soc. 1993, 115, 3056-3065. (f) Boger, D. L.; Yun, W.; Terashima, S. Fukuda, Y.; Nakatani, K.; Kitos, P.; Jin, Q. Bioorg. Med. Chem. Lett. 1992, 2, 759-765.
    • (1994) J. Am. Chem. Soc. , vol.116 , pp. 7996-8006
    • Borger, D.L.1    Yun, W.2
  • 20
    • 0028095610 scopus 로고
    • For recent examples of different DNA alkylation properties of drug enantiomers, see: (a) Boger, D. L.; McKie, J. A.; Nishi, T.; Ogiku, T. J. Am. Chem. Soc. 1997, 119, 311-325. (b) Patel, V. F.; Andis, S. L.; Enkema, J. K.; Johnson, D. A.; Kennedy, J. H.; Mohamadi, F.; Schultz, R. M.; Soose, D. J.; Spees, M. M. J. Org. Chem. 1997, 62, 8868-8874. Borger, D. L.; Yun, W. J. Am. Chem. Soc. 1994, 116, 7996-8006. (d) Boger, D. L.; Johnson, D. S.; Yun, W. J. Am. Chem. Soc. 1994, 116, 1635-1656. (e) Kigoshi, H.; Imamura, Y.; Mizuta, K.; Niwa, H.; Yamada, K. J. Am. Chem. Soc. 1993, 115, 3056-3065. (f) Boger, D. L.; Yun, W.; Terashima, S. Fukuda, Y.; Nakatani, K.; Kitos, P.; Jin, Q. Bioorg. Med. Chem. Lett. 1992, 2, 759-765.
    • (1994) J. Am. Chem. Soc. , vol.116 , pp. 1635-1656
    • Boger, D.L.1    Johnson, D.S.2    Yun, W.3
  • 21
    • 0001290250 scopus 로고
    • For recent examples of different DNA alkylation properties of drug enantiomers, see: (a) Boger, D. L.; McKie, J. A.; Nishi, T.; Ogiku, T. J. Am. Chem. Soc. 1997, 119, 311-325. (b) Patel, V. F.; Andis, S. L.; Enkema, J. K.; Johnson, D. A.; Kennedy, J. H.; Mohamadi, F.; Schultz, R. M.; Soose, D. J.; Spees, M. M. J. Org. Chem. 1997, 62, 8868-8874. Borger, D. L.; Yun, W. J. Am. Chem. Soc. 1994, 116, 7996-8006. Boger, D. L.; Johnson, D. S.; Yun, W. J. Am. Chem. Soc. 1994, 116, 1635-1656. (e) Kigoshi, H.; Imamura, Y.; Mizuta, K.; Niwa, H.; Yamada, K. J. Am. Chem. Soc. 1993, 115, 3056-3065. (f) Boger, D. L.; Yun, W.; Terashima, S. Fukuda, Y.; Nakatani, K.; Kitos, P.; Jin, Q. Bioorg. Med. Chem. Lett. 1992, 2, 759-765.
    • (1993) J. Am. Chem. Soc. , vol.115 , pp. 3056-3065
    • Kigoshi, H.1    Imamura, Y.2    Mizuta, K.3    Niwa, H.4    Yamada, K.5
  • 22
    • 0026646153 scopus 로고
    • For recent examples of different DNA alkylation properties of drug enantiomers, see: (a) Boger, D. L.; McKie, J. A.; Nishi, T.; Ogiku, T. J. Am. Chem. Soc. 1997, 119, 311-325. (b) Patel, V. F.; Andis, S. L.; Enkema, J. K.; Johnson, D. A.; Kennedy, J. H.; Mohamadi, F.; Schultz, R. M.; Soose, D. J.; Spees, M. M. J. Org. Chem. 1997, 62, 8868-8874. Borger, D. L.; Yun, W. J. Am. Chem. Soc. 1994, 116, 7996-8006. Boger, D. L.; Johnson, D. S.; Yun, W. J. Am. Chem. Soc. 1994, 116, 1635-1656. (e) Kigoshi, H.; Imamura, Y.; Mizuta, K.; Niwa, H.; Yamada, K. J. Am. Chem. Soc. 1993, 115, 3056-3065. (f) Boger, D. L.; Yun, W.; Terashima, S. Fukuda, Y.; Nakatani, K.; Kitos, P.; Jin, Q. Bioorg. Med. Chem. Lett. 1992, 2, 759-765.
    • (1992) Bioorg. Med. Chem. Lett. , vol.2 , pp. 759-765
    • Boger, D.L.1    Yun, W.2    Terashima, S.3    Fukuda, Y.4    Nakatani, K.5    Kitos, P.6    Jin, Q.7
  • 24
    • 3643143770 scopus 로고    scopus 로고
    • 15 of 13R-3 and 3′ side G N7 in GG·13R-3 complex obtained by MD simulation was 5.08 Å (0.52)
    • 15 of 13R-3 and 3′ side G N7 in GG·13R-3 complex obtained by MD simulation was 5.08 Å (0.52).
  • 25
    • 3643061391 scopus 로고    scopus 로고
    • Energy calculations at the B3LYP/6-31G(d) level with Gaussian 94 were carried out on a VPP300/16 supercomputer at the JST supercomputer complex
    • Energy calculations at the B3LYP/6-31G(d) level with Gaussian 94 were carried out on a VPP300/16 supercomputer at the JST supercomputer complex.


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