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Issue 8, 2008
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2′-Deoxyimmunosine: stereoselective synthesis, base pairing and duplex stability of oligonucleotides containing 8-oxo-7-thiaguanine

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Abstract

Oligonucleotides containing 7-thia-8-oxoguanine represent a new class of molecules in which sulfur replaces the 7-nitrogen of a purine base. The monomeric 7-thia-8-oxoguanine 2′-deoxyribonucleoside (2′-deoxyimmunosine, 4) was prepared by nucleobase anion glycosylation in a regio- and stereoselective way employing 5-{[(di-n-butylamino)methylidene]amino}thiazolo[4,5-d]pyrimidine-2,7(3H,6H)-dione (18) and 1-chloro-2-deoxy-3,5-di-O-p-toluoyl-α-D-erythro-pentofuranose (6). The nucleoside was converted into the phosphoramidite 22 and oligonucleotides were prepared by solid-phase synthesis. Oligonucleotide duplexes containing the 4–dC base pair show a similar stability as those containing the dG–dC motif. Thus the sterically demanding sulfur and the additional 8-oxo group are well accommodated in the major groove of DNA. As expected, compound 4 does not form a Hoogsteen pair, as reported for 8-oxo-2′-deoxyguanosine. Compared to 2′-deoxyguanosine, 2′-deoxyimmunosine shows a better mismatch discrimination in Watson–Crick base pairs.

Graphical abstract: 2′-Deoxyimmunosine: stereoselective synthesis, base pairing and duplex stability of oligonucleotides containing 8-oxo-7-thiaguanine

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Publication details

The article was received on 29 Nov 2007, accepted on 23 Jan 2008 and first published on 07 Mar 2008


Article type: Paper
DOI: 10.1039/B718500F
Org. Biomol. Chem., 2008,6, 1450-1461

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    2′-Deoxyimmunosine: stereoselective synthesis, base pairing and duplex stability of oligonucleotides containing 8-oxo-7-thiaguanine

    F. Seela and X. Ming, Org. Biomol. Chem., 2008, 6, 1450
    DOI: 10.1039/B718500F

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