1029976-35-9Relevant academic research and scientific papers
2′-Deoxyimmunosine: Stereoselective synthesis, base pairing and duplex stability of oligonucleotides containing 8-oxo-7-thiaguanine
Seela, Frank,Ming, Xin
experimental part, p. 1450 - 1461 (2008/10/09)
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 employing5-{[(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. The Royal Society of Chemistry.
