2 `-deoxyimmunosine: stereoselective synthesis, base pairing and duplex stability of oligonucleotides containing 8-oxo-7-thiaguanine
DC Element | Wert | Sprache |
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dc.contributor.author | Seela, Frank | |
dc.contributor.author | Ming, Xin | |
dc.date.accessioned | 2021-12-23T16:06:11Z | - |
dc.date.available | 2021-12-23T16:06:11Z | - |
dc.date.issued | 2008 | |
dc.identifier.issn | 14770520 | |
dc.identifier.uri | https://osnascholar.ub.uni-osnabrueck.de/handle/unios/7301 | - |
dc.description.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-alpha-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. | |
dc.language.iso | en | |
dc.publisher | ROYAL SOC CHEMISTRY | |
dc.relation.ispartof | ORGANIC & BIOMOLECULAR CHEMISTRY | |
dc.subject | 7-THIA-8-OXOGUANOSINE | |
dc.subject | ANTIVIRAL ACTIVITY | |
dc.subject | BUILDING-BLOCKS | |
dc.subject | C-13 NMR | |
dc.subject | Chemistry | |
dc.subject | Chemistry, Organic | |
dc.subject | DERIVATIVES | |
dc.subject | DNA | |
dc.subject | ISOGUANINE-CYTOSINE | |
dc.subject | NUCLEOSIDE ANALOGS | |
dc.subject | THIAZOLO<4,5-D>PYRIMIDINE RING-SYSTEM | |
dc.subject | VIRUS-INFECTIONS | |
dc.title | 2 `-deoxyimmunosine: stereoselective synthesis, base pairing and duplex stability of oligonucleotides containing 8-oxo-7-thiaguanine | |
dc.type | journal article | |
dc.identifier.doi | 10.1039/b718500f | |
dc.identifier.isi | ISI:000254634200017 | |
dc.description.volume | 6 | |
dc.description.issue | 8 | |
dc.description.startpage | 1450 | |
dc.description.endpage | 1461 | |
dc.contributor.orcid | 0000-0002-7259-1212 | |
dc.publisher.place | THOMAS GRAHAM HOUSE, SCIENCE PARK, MILTON RD, CAMBRIDGE CB4 0WF, CAMBS, ENGLAND | |
dcterms.isPartOf.abbreviation | Org. Biomol. Chem. |
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geprüft am 29.05.2024