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Volumn 4, Issue 24, 2002, Pages 4209-4212

Synthesis, incorporation into triplex-forming oligonucleotide, and binding properties of a novel 2′-deoxy-C-nucleoside featuring a 6-(Thiazolyl-5)benzimidazole nucleobase

Author keywords

[No Author keywords available]

Indexed keywords

6 (THIAZOLYL 5)BENZIMIDAZOLE; 6-(THIAZOLYL-5)BENZIMIDAZOLE; ADENINE; BENZIMIDAZOLE DERIVATIVE; DNA; NUCLEOSIDE; OLIGONUCLEOTIDE; THYMINE; TRIPLEX DNA;

EID: 0037191631     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol026609h     Document Type: Article
Times cited : (46)

References (41)
  • 1
    • 0041866120 scopus 로고    scopus 로고
    • The symbols ·and x indicate Watson-Crick and Hoogsteen hydrogen bonds, respectively
    • The symbols ·and x indicate Watson-Crick and Hoogsteen hydrogen bonds, respectively.
  • 16
    • 0033118865 scopus 로고    scopus 로고
    • and references therein
    • (c) Gowers, D. M.; Fox, K. R. Nucleic Acids Res. 1999, 27, 1569-1577 and references therein.
    • (1999) Nucleic Acids Res. , vol.27 , pp. 1569-1577
    • Gowers, D.M.1    Fox, K.R.2
  • 25
    • 0020972939 scopus 로고
    • For reviews on the chemistry, biochemistry, and synthesis of C-nucleosides analogues, see: (a) Buchanan, J. G. Prog. Chem. Org. Nat. Prod. 1983, 44, 243-299.
    • (1983) Prog. Chem. Org. Nat. Prod. , vol.44 , pp. 243-299
    • Buchanan, J.G.1
  • 28
  • 35
    • 0042868175 scopus 로고    scopus 로고
    • note
    • 13C NMR spectra, we only used the 6-isomer in the next steps of our synthesis.
  • 37
    • 0042868174 scopus 로고    scopus 로고
    • We have verified that this lithiation occurred exclusively and quantitatively at the C-2 position of the benzimidazole moiety by trapping the lithio derivatives with hexachloroethane
    • We have verified that this lithiation occurred exclusively and quantitatively at the C-2 position of the benzimidazole moiety by trapping the lithio derivatives with hexachloroethane.
  • 39
    • 0042367089 scopus 로고    scopus 로고
    • The R and S configurations of compounds 8 and 9 were determined on the basis of the anomeric stereochemistry of their cyclized products 12 and 13, respectively (NOESY experiments)
    • The R and S configurations of compounds 8 and 9 were determined on the basis of the anomeric stereochemistry of their cyclized products 12 and 13, respectively (NOESY experiments).
  • 40
    • 0042868173 scopus 로고    scopus 로고
    • note
    • 2-type mechanism for the outcome of this reaction.
  • 41
    • 0041866119 scopus 로고    scopus 로고
    • note
    • In the same way, we observed for the other anomers (12(α) and 13(α) obtained from 10R and 11R, respectively) clear NOE H1′-H3′ and H1′-H5′ correlations, in accordance with an α configuration.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.