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Volumn 119, Issue 45, 1997, Pages 10909-10919

Facile and selective electrostatic stabilization of uracil N(1)- anion by a proximate protonated amine: A chemical implication for why uracil N(1) is chosen for glycosylation site

Author keywords

[No Author keywords available]

Indexed keywords

AMINE; ANION; URACIL; URACIL DNA GLYCOSYLTRANSFERASE;

EID: 0030669204     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja972129n     Document Type: Article
Times cited : (50)

References (68)
  • 3
    • 0001393273 scopus 로고
    • Frey, P. A. Science 1995, 269, 104-106.
    • (1995) Science , vol.269 , pp. 104-106
    • Frey, P.A.1
  • 14
    • 0025763437 scopus 로고
    • (b) Knowles, J. R. Nature 1991, 350, 121-124.
    • (1991) Nature , vol.350 , pp. 121-124
    • Knowles, J.R.1
  • 18
    • 16944363457 scopus 로고    scopus 로고
    • note
    • In ordinary chemical reactions of uracil, N(3) and N(1) or both are readily alkylated. For specific N(1) alkylation (e.g., glycosylation), N(3)H should be protected as a C(4)-O-silylated form, for example. It may be simply argued that the enzymes stereoselectively hold uracil so that only the N(1) site is available for a nucleophile.
  • 24
    • 0000481993 scopus 로고
    • Boschke, F. L., Ed.; Springer-Verlag: New York
    • Review: Kimura, E. In Topics in Current Chemistry; Boschke, F. L., Ed.; Springer-Verlag: New York, 1985; Vol. 128, pp 113-141.
    • (1985) Topics in Current Chemistry , vol.128 , pp. 113-141
    • Kimura, E.1
  • 29
    • 16944364221 scopus 로고    scopus 로고
    • note
    • - (20%).
  • 31
    • 1442358769 scopus 로고
    • John Wiley & Sons: New York; Chapter 4
    • (b) Conners, K. A. In Binding Constants; John Wiley & Sons: New York, 1987; Chapter 4, p 141.
    • (1987) Binding Constants , pp. 141
    • Conners, K.A.1
  • 52
    • 16944366885 scopus 로고    scopus 로고
    • note
    • a value for N(1)H in the N(3)H-protected (as an 4-enolether) 16 was reported to be 10.7 (ref 8).
  • 53
    • 16944362260 scopus 로고    scopus 로고
    • note
    • - anion in the complexes. These interactions could be more dramatic in a lower dielectric media at an enzyme active site.
  • 54
    • 16944365450 scopus 로고    scopus 로고
    • note
    • + but not from the amide moiety to yield the 20-like species (ref 20).
  • 55
    • 16944366611 scopus 로고    scopus 로고
    • note
    • 2+-cyclen-attached dansylamide 15 was 5.0 (ref 20).
  • 59
    • 0027236428 scopus 로고
    • 2+-cyclen, which showed UV absorption maximum at 265 nm with ∈ = 5930. (a) Shionoya, M; Kimura, E.; Shiro, M. J. Am. Chem. Soc. 1993, 115, 6730-6737. (b) Shionoya, M; Ikeda, T.; Kimura, E.; Shiro, M. J. Am. Chem. Soc. 1994, 116, 3848-3859. (c) Shionoya, M.; Sugiyama, M.; Kimura, E. J. Chem. Soc., Chem. Commun. 1994, 1747-1748. (d) Tucker, J. H. R.; Shionoya, M.; Koike, T.; Kimura, E. Bull. Chem. Soc. Jpn. 1995, 68, 2465-2469. (e) Koike, T.; Takashige, M.; Kimura, E.; Fujioka, H.; Shiro, M. Chem. Eur. J. 1996, 2, 617-623. (f) Fujioka, H.; Koike, T.; Yamada, N.; Kimura, E. Heterocycles 1996, 42, 775-787.
    • (1993) J. Am. Chem. Soc. , vol.115 , pp. 6730-6737
    • Shionoya, M.1    Kimura, E.2    Shiro, M.3
  • 60
    • 0028180563 scopus 로고
    • 2+-cyclen, which showed UV absorption maximum at 265 nm with ∈ = 5930. (a) Shionoya, M; Kimura, E.; Shiro, M. J. Am. Chem. Soc. 1993, 115, 6730-6737. (b) Shionoya, M; Ikeda, T.; Kimura, E.; Shiro, M. J. Am. Chem. Soc. 1994, 116, 3848-3859. (c) Shionoya, M.; Sugiyama, M.; Kimura, E. J. Chem. Soc., Chem. Commun. 1994, 1747-1748. (d) Tucker, J. H. R.; Shionoya, M.; Koike, T.; Kimura, E. Bull. Chem. Soc. Jpn. 1995, 68, 2465-2469. (e) Koike, T.; Takashige, M.; Kimura, E.; Fujioka, H.; Shiro, M. Chem. Eur. J. 1996, 2, 617-623. (f) Fujioka, H.; Koike, T.; Yamada, N.; Kimura, E. Heterocycles 1996, 42, 775-787.
    • (1994) J. Am. Chem. Soc. , vol.116 , pp. 3848-3859
    • Shionoya, M.1    Ikeda, T.2    Kimura, E.3    Shiro, M.4
  • 61
    • 0027990690 scopus 로고
    • 2+-cyclen, which showed UV absorption maximum at 265 nm with ∈ = 5930. (a) Shionoya, M; Kimura, E.; Shiro, M. J. Am. Chem. Soc. 1993, 115, 6730-6737. (b) Shionoya, M; Ikeda, T.; Kimura, E.; Shiro, M. J. Am. Chem. Soc. 1994, 116, 3848-3859. (c) Shionoya, M.; Sugiyama, M.; Kimura, E. J. Chem. Soc., Chem. Commun. 1994, 1747-1748. (d) Tucker, J. H. R.; Shionoya, M.; Koike, T.; Kimura, E. Bull. Chem. Soc. Jpn. 1995, 68, 2465-2469. (e) Koike, T.; Takashige, M.; Kimura, E.; Fujioka, H.; Shiro, M. Chem. Eur. J. 1996, 2, 617-623. (f) Fujioka, H.; Koike, T.; Yamada, N.; Kimura, E. Heterocycles 1996, 42, 775-787.
    • (1994) J. Chem. Soc., Chem. Commun. , pp. 1747-1748
    • Shionoya, M.1    Sugiyama, M.2    Kimura, E.3
  • 62
    • 0000722487 scopus 로고
    • 2+-cyclen, which showed UV absorption maximum at 265 nm with ∈ = 5930. (a) Shionoya, M; Kimura, E.; Shiro, M. J. Am. Chem. Soc. 1993, 115, 6730-6737. (b) Shionoya, M; Ikeda, T.; Kimura, E.; Shiro, M. J. Am. Chem. Soc. 1994, 116, 3848-3859. (c) Shionoya, M.; Sugiyama, M.; Kimura, E. J. Chem. Soc., Chem. Commun. 1994, 1747-1748. (d) Tucker, J. H. R.; Shionoya, M.; Koike, T.; Kimura, E. Bull. Chem. Soc. Jpn. 1995, 68, 2465-2469. (e) Koike, T.; Takashige, M.; Kimura, E.; Fujioka, H.; Shiro, M. Chem. Eur. J. 1996, 2, 617-623. (f) Fujioka, H.; Koike, T.; Yamada, N.; Kimura, E. Heterocycles 1996, 42, 775-787.
    • (1995) Bull. Chem. Soc. Jpn. , vol.68 , pp. 2465-2469
    • Tucker, J.H.R.1    Shionoya, M.2    Koike, T.3    Kimura, E.4
  • 63
    • 0001013083 scopus 로고    scopus 로고
    • 2+-cyclen, which showed UV absorption maximum at 265 nm with ∈ = 5930. (a) Shionoya, M; Kimura, E.; Shiro, M. J. Am. Chem. Soc. 1993, 115, 6730-6737. (b) Shionoya, M; Ikeda, T.; Kimura, E.; Shiro, M. J. Am. Chem. Soc. 1994, 116, 3848-3859. (c) Shionoya, M.; Sugiyama, M.; Kimura, E. J. Chem. Soc., Chem. Commun. 1994, 1747-1748. (d) Tucker, J. H. R.; Shionoya, M.; Koike, T.; Kimura, E. Bull. Chem. Soc. Jpn. 1995, 68, 2465-2469. (e) Koike, T.; Takashige, M.; Kimura, E.; Fujioka, H.; Shiro, M. Chem. Eur. J. 1996, 2, 617-623. (f) Fujioka, H.; Koike, T.; Yamada, N.; Kimura, E. Heterocycles 1996, 42, 775-787.
    • (1996) Chem. Eur. J. , vol.2 , pp. 617-623
    • Koike, T.1    Takashige, M.2    Kimura, E.3    Fujioka, H.4    Shiro, M.5
  • 64
    • 0000474926 scopus 로고    scopus 로고
    • 2+-cyclen, which showed UV absorption maximum at 265 nm with ∈ = 5930. (a) Shionoya, M; Kimura, E.; Shiro, M. J. Am. Chem. Soc. 1993, 115, 6730-6737. (b) Shionoya, M; Ikeda, T.; Kimura, E.; Shiro, M. J. Am. Chem. Soc. 1994, 116, 3848-3859. (c) Shionoya, M.; Sugiyama, M.; Kimura, E. J. Chem. Soc., Chem. Commun. 1994, 1747-1748. (d) Tucker, J. H. R.; Shionoya, M.; Koike, T.; Kimura, E. Bull. Chem. Soc. Jpn. 1995, 68, 2465-2469. (e) Koike, T.; Takashige, M.; Kimura, E.; Fujioka, H.; Shiro, M. Chem. Eur. J. 1996, 2, 617-623. (f) Fujioka, H.; Koike, T.; Yamada, N.; Kimura, E. Heterocycles 1996, 42, 775-787.
    • (1996) Heterocycles , vol.42 , pp. 775-787
    • Fujioka, H.1    Koike, T.2    Yamada, N.3    Kimura, E.4


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.