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Volumn 72, Issue 3, 2007, Pages 805-815

Solid-phase synthesis of thermolytic DNA oligonucleotides functionalized with a single 4-hydroxy-1-butyl or 4-phosphato-/thiophosphato-1-butyl thiophosphate protecting group

Author keywords

[No Author keywords available]

Indexed keywords

OLIGONUCLEOTIDES; PHOSPHORAMIDITES; PHOSPHORYLATION; SOLID PHASE SYNTHESIS;

EID: 33846935981     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo062087y     Document Type: Article
Times cited : (20)

References (54)
  • 18
    • 33846910154 scopus 로고    scopus 로고
    • The CPS(FMA)GPS(FMA) sequence within the 5′-proximal GPS(FMA)APS(FMA)C PS(FMA)GPS(FMA)TPS(FMA)T motif is critical for bioactivity in vivo. Replacing CPS(FMA)GPS(FMA) of the motif with GPS(FMA)GPS(FMA, ODN fma1556) results in complete suppression of the immunostimulatory properties of CpG ODN fma1555 in mice see ref 5a
    • PS(FMA) (ODN fma1556) results in complete suppression of the immunostimulatory properties of CpG ODN fma1555 in mice (see ref 5a).
  • 19
    • 33846921470 scopus 로고    scopus 로고
    • The maximum concentration of CpG ODN fma1555 obtainable in water is ∼1 mM.
    • The maximum concentration of CpG ODN fma1555 obtainable in water is ∼1 mM.
  • 23
    • 33846928393 scopus 로고    scopus 로고
    • Wilk, A.; Grajkowski, A.; Chmielewski, M. K.; Phillips, L. R.; Beaucage, S. L. In Current Protocols in Nucleic Acid Chemistry; Beaucage, S. L., Bergstrom, D. E., Glick, G. D., Jones, R. A., Eds.; John Wiley & Sons: New York, 2001; I, pp 2.7.1-2.7.12.
    • (d) Wilk, A.; Grajkowski, A.; Chmielewski, M. K.; Phillips, L. R.; Beaucage, S. L. In Current Protocols in Nucleic Acid Chemistry; Beaucage, S. L., Bergstrom, D. E., Glick, G. D., Jones, R. A., Eds.; John Wiley & Sons: New York, 2001; Vol. I, pp 2.7.1-2.7.12.
  • 28
    • 33846898907 scopus 로고    scopus 로고
    • Wilk, A.; Chmielewski, M. K.; Grajkowski, A.; Phillips, L. R.; Beaucage, S. L. In Current Protocols in Nucleic Acid Chemistry; Beaucage, S. L., Bergstrom, D. E., Glick, G. D., Jones, R. A., Eds.; John Wiley & Sons: New York, 2002; I, pp 3.9.1-3.9.16.
    • (e) Wilk, A.; Chmielewski, M. K.; Grajkowski, A.; Phillips, L. R.; Beaucage, S. L. In Current Protocols in Nucleic Acid Chemistry; Beaucage, S. L., Bergstrom, D. E., Glick, G. D., Jones, R. A., Eds.; John Wiley & Sons: New York, 2002; Vol. I, pp 3.9.1-3.9.16.
  • 31
    • 33846905660 scopus 로고    scopus 로고
    • Even though only 7a, 8a, and 8b are required for the present work, phosphoramidites 8c,d were also prepared and characterized for use in experiments that are beyond the scope of this report.
    • Even though only 7a, 8a, and 8b are required for the present work, phosphoramidites 8c,d were also prepared and characterized for use in experiments that are beyond the scope of this report.
  • 33
    • 33846906631 scopus 로고    scopus 로고
    • 31P NMR spectra of 7a and 8a-d are presented in the SI.
    • 31P NMR spectra of 7a and 8a-d are presented in the SI.
  • 39
    • 33846914796 scopus 로고    scopus 로고
    • PST are shown in Chart 1 of the SI.
    • PST are shown in Chart 1 of the SI.
  • 43
    • 33846898679 scopus 로고    scopus 로고
    • RP-HPLC chromatogram of the dinucleotide is shown in Chart 13A of the SI.
    • RP-HPLC chromatogram of the dinucleotide is shown in Chart 13A of the SI.
  • 44
    • 33846924959 scopus 로고    scopus 로고
    • This statement is substantiated by the rapid and homologous conversion of dinucleotide 6a to the hydroxybutylated dinucleotide 4 upon reaction with human alkaline phosphatase at 37°C
    • This statement is substantiated by the rapid and homologous conversion of dinucleotide 6a to the hydroxybutylated dinucleotide 4 upon reaction with human alkaline phosphatase at 37°C.
  • 46
    • 33846894678 scopus 로고    scopus 로고
    • Stawinski, J.; Strömberg, R. In Current Protocols in Nucleic Acid Chemistry; Beaucage, S. L., Bergstrom, D. E., Glick, G. D., Jones, R. A., Eds.; John Wiley & Sons: New York, 2001; pp 2.6.1-2.6.15 and references therein.
    • Stawinski, J.; Strömberg, R. In Current Protocols in Nucleic Acid Chemistry; Beaucage, S. L., Bergstrom, D. E., Glick, G. D., Jones, R. A., Eds.; John Wiley & Sons: New York, 2001; pp 2.6.1-2.6.15 and references therein.
  • 51
    • 33846895342 scopus 로고    scopus 로고
    • Only hydrazinolysis was effective in the cleavage of the levulinyl group within an acceptable period of time at ∼25°C
    • Only hydrazinolysis was effective in the cleavage of the levulinyl group within an acceptable period of time at ∼25°C.
  • 54
    • 33846904686 scopus 로고    scopus 로고
    • To ensure optimal formation of 8d, the reaction time was extended to 16 h at ∼25°C.
    • To ensure optimal formation of 8d, the reaction time was extended to 16 h at ∼25°C.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.