8-Aza-2 `-deoxyguanosine: Base pairing, mismatch discrimination and nucleobase anion fluorescence sensing in single-stranded and duplex DNA
DC Element | Wert | Sprache |
---|---|---|
dc.contributor.author | Seela, Frank | |
dc.contributor.author | Jiang, Dawei | |
dc.contributor.author | Xu, Kuiying | |
dc.date.accessioned | 2021-12-23T16:05:42Z | - |
dc.date.available | 2021-12-23T16:05:42Z | - |
dc.date.issued | 2009 | |
dc.identifier.issn | 14770520 | |
dc.identifier.uri | https://osnascholar.ub.uni-osnabrueck.de/handle/unios/7153 | - |
dc.description.abstract | Oligodeoxyribonucleotides containing 8-aza-2'-deoxyguanosine 9 were synthesized and a new phosphoramidite 11, showing a high coupling yield in solid-phase synthesis, was prepared. Nucleoside 9 was found to be a perfect shape mimic of dG; it forms a strong base pair with dC and shows an excellent mismatch discrimination. Nucleoside 9 appears strongly fluorescent as the anion, and thus, it has unique reporter group properties as a replacement for dG. The pK(a)-value of 9 (8.4) is lower than that of dG (9.3) and increases from the single-stranded DNA (8.8) to duplex DNA (9.1). The fluorescence of the nucleoside 9 anion is decreased in ss-oligonucleotides and further reduced in duplex DNA. When mismatches of 9 are formed with the four DNA canonical bases, the fluorescence of mismatches is significantly higher than that of the perfectly paired duplex. The fluorescence of the nucleoside 9 anion correlates with the base pair stability. | |
dc.description.sponsorship | Roche Diagnostics GmbH; Penzberg; ChemBiotech, Munster, Germany; We thank Mr. N. Q. Tran for the oligonucleotide synthesis andDr. T. Koch from Roche Diagnostics, Penzberg, for the measurement of the MALDI spectra. We appreciate critical reading of the manuscript by Dr. P. Leonard, Dr. S. Budow and Mr. S. Pujari. Financial support by Roche Diagnostics GmbH, Penzberg, and ChemBiotech, Munster, Germany, is gratefully acknowledged. | |
dc.language.iso | en | |
dc.publisher | ROYAL SOC CHEMISTRY | |
dc.relation.ispartof | ORGANIC & BIOMOLECULAR CHEMISTRY | |
dc.subject | 2-AMINOPURINE | |
dc.subject | 8-AZAPURINES | |
dc.subject | ANALOGS | |
dc.subject | BENZOTRIAZOLE | |
dc.subject | Chemistry | |
dc.subject | Chemistry, Organic | |
dc.subject | EMISSION PROPERTIES | |
dc.subject | GUANOSINE | |
dc.subject | NUCLEOSIDE | |
dc.subject | OLIGODEOXYNUCLEOTIDES | |
dc.subject | PYRROLO-C | |
dc.title | 8-Aza-2 `-deoxyguanosine: Base pairing, mismatch discrimination and nucleobase anion fluorescence sensing in single-stranded and duplex DNA | |
dc.type | journal article | |
dc.identifier.doi | 10.1039/b908017a | |
dc.identifier.isi | ISI:000268975300016 | |
dc.description.volume | 7 | |
dc.description.issue | 17 | |
dc.description.startpage | 3463 | |
dc.description.endpage | 3473 | |
dc.identifier.eissn | 14770539 | |
dc.publisher.place | THOMAS GRAHAM HOUSE, SCIENCE PARK, MILTON RD, CAMBRIDGE CB4 0WF, CAMBS, ENGLAND | |
dcterms.isPartOf.abbreviation | Org. Biomol. Chem. |
Seitenaufrufe
2
Letzte Woche
0
0
Letzter Monat
0
0
geprüft am 07.06.2024