Incorporation of 2'-Deoxy-6-thioguanosine into G-Rich Oligodeoxyribonucleotides Inhibits G-Tetrad Formation and Facilitates Triplex Formation

An efficient and expeditious method for the synthesis of S6-(cyanoethyl)-N2-isobutyryl (or trifluoroacetyl)-2'-deoxy-6-thioguanosine (7 and 2) from 2'-deoxyguanosine (G) has been developed. Compound 7 has been incorporated into several G-rich triple-helix-forming oligonucleotides (TFOs) us...

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Bibliographic Details
Published in:Biochemistry (Easton) 1995, Vol.34 (3), p.765-772
Main Authors: Rao, T. Sudhakar, Durland, Ross H, Seth, Dale M, Myrick, Melissa A, Bodepudi, Veeraiah, Revankar, Ganapathi R
Format: Article
Language:English
Subjects:
Base Sequence
Deoxyguanosine - analogs & derivatives
Deoxyguanosine - chemistry
Hydrogen Bonding
Molecular Sequence Data
Nucleic Acid Conformation
Oligodeoxyribonucleotides - chemistry
Structure-Activity Relationship
Thionucleosides - chemistry
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Summary:An efficient and expeditious method for the synthesis of S6-(cyanoethyl)-N2-isobutyryl (or trifluoroacetyl)-2'-deoxy-6-thioguanosine (7 and 2) from 2'-deoxyguanosine (G) has been developed. Compound 7 has been incorporated into several G-rich triple-helix-forming oligonucleotides (TFOs) using solid-support, phosphoramidite chemistry. The purified oligonucleotides containing 2'-deoxy-6-thioguanosine (S6-dG) residues in the place of G have been characterized by nucleoside composition analysis. These modified TFOs have been shown to be stable in aqueous, as well as buffered, solutions normally used to assay triple-helix formation. It has also been demonstrated that partial incorporation of S6-dG is effective in inhibiting the formation of G tetrads in G-rich oligodeoxyribonucleotides, thus facilitating triple-helix formation in potassium-containing buffers.
ISSN:0006-2960
1520-4995
DOI:10.1021/bi00003a009