8-Aza-2 `-deoxyguanosine: Base pairing, mismatch discrimination and nucleobase anion fluorescence sensing in single-stranded and duplex DNA

DC FieldValueLanguage
dc.contributor.authorSeela, Frank
dc.contributor.authorJiang, Dawei
dc.contributor.authorXu, Kuiying
dc.date.accessioned2021-12-23T16:05:42Z-
dc.date.available2021-12-23T16:05:42Z-
dc.date.issued2009
dc.identifier.issn14770520
dc.identifier.urihttps://osnascholar.ub.uni-osnabrueck.de/handle/unios/7153-
dc.description.abstractOligodeoxyribonucleotides 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.sponsorshipRoche 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.isoen
dc.publisherROYAL SOC CHEMISTRY
dc.relation.ispartofORGANIC & BIOMOLECULAR CHEMISTRY
dc.subject2-AMINOPURINE
dc.subject8-AZAPURINES
dc.subjectANALOGS
dc.subjectBENZOTRIAZOLE
dc.subjectChemistry
dc.subjectChemistry, Organic
dc.subjectEMISSION PROPERTIES
dc.subjectGUANOSINE
dc.subjectNUCLEOSIDE
dc.subjectOLIGODEOXYNUCLEOTIDES
dc.subjectPYRROLO-C
dc.title8-Aza-2 `-deoxyguanosine: Base pairing, mismatch discrimination and nucleobase anion fluorescence sensing in single-stranded and duplex DNA
dc.typejournal article
dc.identifier.doi10.1039/b908017a
dc.identifier.isiISI:000268975300016
dc.description.volume7
dc.description.issue17
dc.description.startpage3463
dc.description.endpage3473
dc.identifier.eissn14770539
dc.publisher.placeTHOMAS GRAHAM HOUSE, SCIENCE PARK, MILTON RD, CAMBRIDGE CB4 0WF, CAMBS, ENGLAND
dcterms.isPartOf.abbreviationOrg. Biomol. Chem.
Show simple item record

Page view(s)

2
Last Week
0
Last month
0
checked on Apr 16, 2024

Google ScholarTM

Check

Altmetric