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Volumn 53, Issue 32, 1997, Pages 11191-11202

6-Thio-2'-deoxyinosine: Synthesis, incorporation, and evaluation as a postsynthetically modifiable base in oligonucleotides

Author keywords

[No Author keywords available]

Indexed keywords

6 THIO 2' DEOXYINOSINE DERIVATIVE; INOSINE DERIVATIVE; OLIGODEOXYNUCLEOTIDE; UNCLASSIFIED DRUG;

EID: 0030748434     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(97)00376-1     Document Type: Article
Times cited : (25)

References (48)
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    • This direct protocol for introduction of the S-cyanoethyl ether was completely unsuccesful with 4-thio2́-deoxyuridine. Under a wide variety of conditions with 4-thio-2́-deoxyuridine we observed consumption of 3-bromopropionitrile without production of the corresponding thioether, indicating that the alkylation was followed by a facile retro Michael reaction to liberate acrylonitrile under the basic reaction conditions (see reference 9)
    • This direct protocol for introduction of the S-cyanoethyl ether was completely unsuccesful with 4-thio2́-deoxyuridine. Under a wide variety of conditions with 4-thio-2́-deoxyuridine we observed consumption of 3-bromopropionitrile without production of the corresponding thioether, indicating that the alkylation was followed by a facile retro Michael reaction to liberate acrylonitrile under the basic reaction conditions (see reference 9).
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    • This strategy has previously been employed for 6-thioguanosine concomitant with S-cyanoethyl deprotection: Christopherson, M. S.; Broom, A. D. Nucleic Acids Res. 1991, 19, 5719.
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    • note
    • 2O, 1:1) to afford 12 and 13, respectively. (formula presented)
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    • Eckstein, F., Ed.; Oxford University Press: New York
    • Extinction coefficients for natural bases: Connolly, B. A., in Oligonucleotides and Analogues; Eckstein, F., Ed.; Oxford University Press: New York; p 180.
    • Oligonucleotides and Analogues , pp. 180
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    • For the successful use of a bis-electrophile in cross-linking reactions, see reference 3
    • For the successful use of a bis-electrophile in cross-linking reactions, see reference 3.
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    • For the origin and design of this side-chain, see reference 3
    • For the origin and design of this side-chain, see reference 3.
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    • All synthetic and post-synthetically modified oligonucleotides were prepared as described in the Experimental Section, and were purified by RP-HPLC to homogeneity
    • All synthetic and post-synthetically modified oligonucleotides were prepared as described in the Experimental Section, and were purified by RP-HPLC to homogeneity.


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