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Volumn 7, Issue 6, 2005, Pages 1165-1168

Syntheses of silatranyl- and germatranyluridines

Author keywords

[No Author keywords available]

Indexed keywords

DEUTERIUM OXIDE; GERMANIUM DERIVATIVE; RHENIUM; RNA; SILATRANE DERIVATIVE; URIDINE DERIVATIVE; VANADIUM;

EID: 18244393748     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol050133v     Document Type: Article
Times cited : (8)

References (42)
  • 13
    • 0033325108 scopus 로고    scopus 로고
    • For reviews, see: (a) Scott, W. G. Q. Rev. Biophys. 1999, 32, 241-284. (b) Hammann, C.; Lilley, D. M. J. ChemBioChem 2002, 3, 690-700.
    • (1999) Q. Rev. Biophys. , vol.32 , pp. 241-284
    • Scott, W.G.1
  • 14
    • 0036903567 scopus 로고    scopus 로고
    • For reviews, see: (a) Scott, W. G. Q. Rev. Biophys. 1999, 32, 241-284. (b) Hammann, C.; Lilley, D. M. J. ChemBioChem 2002, 3, 690-700.
    • (2002) ChemBioChem , vol.3 , pp. 690-700
    • Hammann, C.1    Lilley, D.M.J.2
  • 15
    • 18244368831 scopus 로고    scopus 로고
    • University of California at Santa Cruz, Santa Cruz, CA. Personal communication
    • Scott, W. G. University of California at Santa Cruz, Santa Cruz, CA. Personal communication, 2004.
    • (2004)
    • Scott, W.G.1
  • 21
    • 18244381649 scopus 로고    scopus 로고
    • ACS Symposium Series 711; American Chemical Society: Washington, DC
    • Vanadium Compounds; Tracey, A. S., Crans, D. C., Eds.; ACS Symposium Series 711; American Chemical Society: Washington, DC, 1998.
    • (1998) Vanadium Compounds
    • Tracey, A.S.1    Crans, D.C.2
  • 28
    • 0001259966 scopus 로고
    • If unmethylated, N-3 is subsequently alkylated by ethylene oxide further into the synthesis (see Supporting Information). The N3-methyl is also believed to provide stability to all of the atranyl-nucleosides (1, 2, 7, and 8). This is due to the fact the 2′-nitrogen is a decent leaving group (it has a formal positive charge) and it is well-known that uridines with leaving groups positioned on the 2′-position are subject to anhydrouridine formation. See Supporting Information and the following reference: Yung, N. C.; Fox, J. J. J. Am. Chem. Soc. 1961, 83, 3060-3066.
    • (1961) J. Am. Chem. Soc. , vol.83 , pp. 3060-3066
    • Yung, N.C.1    Fox, J.J.2
  • 33
    • 18244390816 scopus 로고    scopus 로고
    • note
    • See Supporting Information for more details.
  • 36
    • 0030752599 scopus 로고    scopus 로고
    • C17 in the hammerhead ribozyme was previously replaced with 3-methyluridine and found to retain much of its catalytic activity, with a cleavage rate equal to 43% of the wt rate; see: Baidya, N.; Animons, G. E.; Matulic-Adamic, J.; Karpeisky, A. M.; Beigelman, L.; Uhlenbeck, O. C. RNA 1997, 3, 1135-1142.
    • (1997) RNA , vol.3 , pp. 1135-1142
    • Baidya, N.1    Animons, G.E.2    Matulic-Adamic, J.3    Karpeisky, A.M.4    Beigelman, L.5    Uhlenbeck, O.C.6
  • 41
    • 0022119102 scopus 로고
    • Although there are several examples of silicon-containing nucleosides, there are just two examples of germanium-containing nucleosides or nucleosidelike compounds, see: (a) Mel'nik, S. I.; Bakhmedova, A. A.; Nedorezova, T. P.; Iartseva, I. V.; Zhukova, O. S. Bioorg. Khim. 1985, 11, 1248-1252. (b) Lukevics, E.; Ignatovich, L.; Shilina, N.; Kemme, A.; Sjakste, N. Metal-Based Drugs 1994, 1, 65-72.
    • (1985) Bioorg. Khim. , vol.11 , pp. 1248-1252
    • Mel'nik, S.I.1    Bakhmedova, A.A.2    Nedorezova, T.P.3    Iartseva, I.V.4    Zhukova, O.S.5
  • 42
    • 0022119102 scopus 로고
    • Although there are several examples of silicon-containing nucleosides, there are just two examples of germanium-containing nucleosides or nucleosidelike compounds, see: (a) Mel'nik, S. I.; Bakhmedova, A. A.; Nedorezova, T. P.; Iartseva, I. V.; Zhukova, O. S. Bioorg. Khim. 1985, 11, 1248-1252. (b) Lukevics, E.; Ignatovich, L.; Shilina, N.; Kemme, A.; Sjakste, N. Metal-Based Drugs 1994, 1, 65-72.
    • (1994) Metal-Based Drugs , vol.1 , pp. 65-72
    • Lukevics, E.1    Ignatovich, L.2    Shilina, N.3    Kemme, A.4    Sjakste, N.5


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.