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Volumn 73, Issue 7, 2008, Pages 2774-2783

The 4-(N-dichloroacetyl-N-methylamino)benzyloxymethyl group for 2′-hydroxyl protection of ribonucleosides in the solid-phase synthesis of oligoribonucleotides

Author keywords

[No Author keywords available]

Indexed keywords

ENZYME ACTIVITY; ORGANIC COMPOUNDS; RNA; SYNTHESIS (CHEMICAL);

EID: 41649103104     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo702717g     Document Type: Article
Times cited : (27)

References (55)
  • 4
    • 33751099034 scopus 로고    scopus 로고
    • For excellent reviews on the mechanistic aspects of RNAi, see: a
    • For excellent reviews on the mechanistic aspects of RNAi, see: (a) Bumcrot, D.; Manoharan, M.; Koteliansky, V.; Sah, D. W. Y. Nature Chem. Biol. 2006, 2, 711-719.
    • (2006) Nature Chem. Biol , vol.2 , pp. 711-719
    • Bumcrot, D.1    Manoharan, M.2    Koteliansky, V.3    Sah, D.W.Y.4
  • 8
    • 0347444723 scopus 로고    scopus 로고
    • Bartel, D. P. Cell 2004, 116, 281-297.
    • (2004) Cell , vol.116 , pp. 281-297
    • Bartel, D.P.1
  • 15
    • 85044900224 scopus 로고    scopus 로고
    • (d) Reese, C. B. Tetrahedron 2002, 58, 8893-8920.
    • (2002) Tetrahedron , vol.58 , pp. 8893-8920
    • Reese, C.B.1
  • 16
    • 41649108690 scopus 로고    scopus 로고
    • Reese, C. B. 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, 2000; I, pp 2.2.1-2.2.24.
    • (e) Reese, C. B. 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, 2000; Vol. I, pp 2.2.1-2.2.24.
  • 17
    • 0011801450 scopus 로고    scopus 로고
    • (f) Pitsch, S. Chimia 2001, 55, 320-324.
    • (2001) Chimia , vol.55 , pp. 320-324
    • Pitsch, S.1
  • 20
    • 41649118511 scopus 로고    scopus 로고
    • Miller, T. J.; Schwartz, M. E.; Gough, G. 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, 2000; I, pp 2.5.1-2.5.36 and pp 3.7.1-3.7.8.
    • (b) Miller, T. J.; Schwartz, M. E.; Gough, G. 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, 2000; Vol. I, pp 2.5.1-2.5.36 and pp 3.7.1-3.7.8.
  • 26
    • 41649084419 scopus 로고    scopus 로고
    • Pitsch, S.; Weiss, P. A. 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 2.9.1-2.9.14 and 3.8.1-3.8.15.
    • (b) Pitsch, S.; Weiss, P. A. 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 2.9.1-2.9.14 and 3.8.1-3.8.15.
  • 35
    • 41649114638 scopus 로고    scopus 로고
    • Scaringe, S. A.; Kitchen, D.; Kaiser, R. J.; Marshall, W. S. 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, 2004; I, pp. 2.10.1-2.10.16.
    • (b) Scaringe, S. A.; Kitchen, D.; Kaiser, R. J.; Marshall, W. S. 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, 2004; Vol. I, pp. 2.10.1-2.10.16.
  • 46
    • 41649089387 scopus 로고    scopus 로고
    • This purification step is critically important. One must ensure that the desired ribonucleoside 2′-acetal is not contaminated with any 3′-acetal to prevent subsequent incorporation of 2′→5′, internucleotidic phosphodiester linkages into the oligoribonucleotide during solid-phase synthesis
    • This purification step is critically important. One must ensure that the desired ribonucleoside 2′-acetal is not contaminated with any 3′-acetal to prevent subsequent incorporation of (2′→5′)- internucleotidic phosphodiester linkages into the oligoribonucleotide during solid-phase synthesis.
  • 49
    • 41649087859 scopus 로고    scopus 로고
    • The RP-HPLC retention time of 29 (tR, 19.6 min) is identical to that of an authentic sample of 4-(N-methylamino)benzyl alcohol that was prepared from the reduction of 4-(N-methylamino)benzoic acid see ref 25
    • R = 19.6 min) is identical to that of an authentic sample of 4-(N-methylamino)benzyl alcohol that was prepared from the reduction of 4-(N-methylamino)benzoic acid (see ref 25).
  • 51
    • 27844454796 scopus 로고    scopus 로고
    • and references therein
    • Reese C.B. Org. Biomol. Chem. 2005, 3, 3851-3868 and references therein.
    • (2005) Org. Biomol. Chem , vol.3 , pp. 3851-3868
    • Reese, C.B.1
  • 52
    • 0027445885 scopus 로고    scopus 로고
    • Synthetic (3′→5′)UpU is a substrate for BSP but synthetic (2′→5′)UpU is not. Data are presented in the Supporting Information. See also: (a) Giannaris, P. A.; Damha, M. J. Nucleic Acids Res. 1993, 21, 4742-4749.
    • Synthetic (3′→5′)UpU is a substrate for BSP but synthetic (2′→5′)UpU is not. Data are presented in the Supporting Information. See also: (a) Giannaris, P. A.; Damha, M. J. Nucleic Acids Res. 1993, 21, 4742-4749.
  • 54
    • 41649098045 scopus 로고    scopus 로고
    • Commercial bovine spleen phosphodiesterase contains some (1% w/w) adenosine deaminase (ADA) as a contaminant. Such a low concentration of ADA in the digestion reaction was sufficient to quantitatively convert adenosine to inosine. This conversion was unambiguously demonstrated by mixing adenosine with BSP/BAP under the conditions used for the digestion of the RNA oligomer. RP-HPLC analysis of the reaction indicated complete conversion of adenosine to inosine, which had a retention time identical to that of a commercial sample of inosine (data shown in the Supporting Information).
    • Commercial bovine spleen phosphodiesterase contains some (1% w/w) adenosine deaminase (ADA) as a contaminant. Such a low concentration of ADA in the digestion reaction was sufficient to quantitatively convert adenosine to inosine. This conversion was unambiguously demonstrated by mixing adenosine with BSP/BAP under the conditions used for the digestion of the RNA oligomer. RP-HPLC analysis of the reaction indicated complete conversion of adenosine to inosine, which had a retention time identical to that of a commercial sample of inosine (data shown in the Supporting Information).
  • 55
    • 41649112167 scopus 로고    scopus 로고
    • 2 is employed as an eluent.
    • 2 is employed as an eluent.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.