Nucleoside and oligonucleotide pyrene conjugates with 1,2,3-triazolyl or ethynyl linkers: synthesis, duplex stability, and fluorescence changes generated by the DNA-dye connector

DC FieldValueLanguage
dc.contributor.authorIngale, Sachin A.
dc.contributor.authorSeela, Frank
dc.date.accessioned2021-12-23T16:06:25Z-
dc.date.available2021-12-23T16:06:25Z-
dc.date.issued2014
dc.identifier.issn00404020
dc.identifier.urihttps://osnascholar.ub.uni-osnabrueck.de/handle/unios/7395-
dc.description.abstractFluorescent nucleosides and oligonucleotides functionalized with pyrene were synthesized using `click' chemistry or the Sonogashira cross-coupling reaction. The dye was connected to position-7 of 7-deaza-2'-deoxyguanosine or to the 2'-deoxyribofuranose moiety. Four different DNA-dye connectors with 1,2,3-triazolyl residues or triple bonds were constructed. Phosphoramidites of the pyrene conjugates (9, 14, 25) were prepared and used in solid-phase synthesis. Short linkers (2, 4) destabilize DNA, while long linkers (1) increased duplex stability. Nucleosides and oligonucleotides with single dye incorporations show linker dependent fluorescence. Linker dependent excimer emission with pyrenes in proximal positions was also observed. A `superchromophore' formed by the 7-deaza-2'-deoxyguanosine ethynylpyrene conjugate shows strong red shifted fluorescence emission at 495 nm. (C) 2013 Elsevier Ltd. All rights reserved.
dc.description.sponsorshipChemBiotech, Munster, Germany; We thank Dr. S. Budow-Busse and Dr. P. Leonard for helpful discussions and support while preparing the manuscript. We also thank Mr. S.S. Pujari and H. Mei for measuring the NMR spectra and Mr. Nhat Quang Tran for the oligonucleotide syntheses. We would like to thank Dr. M. Letzel, Organisch-Chemisches Institut, Universitat Munster, Germany, for the measurement of the MALDI spectra. Financial support by ChemBiotech, Munster, Germany, is highly appreciated.
dc.language.isoen
dc.publisherPERGAMON-ELSEVIER SCIENCE LTD
dc.relation.ispartofTETRAHEDRON
dc.subjectChemistry
dc.subjectChemistry, Organic
dc.subjectCYTOSINE
dc.subjectDNA
dc.subjectDuplex stability
dc.subjectELECTRON-TRANSFER
dc.subjectEXCIMER FLUORESCENCE
dc.subjectFluorescence
dc.subjectHYBRIDIZATION
dc.subjectMOLECULAR BEACON
dc.subjectMONOMER FLUORESCENCE
dc.subjectNUCLEIC-ACIDS
dc.subjectNUCLEOBASE
dc.subjectNucleosides
dc.subjectPyrene linker
dc.subjectQUENCHER-FREE
dc.subjectSIDE-CHAINS
dc.titleNucleoside and oligonucleotide pyrene conjugates with 1,2,3-triazolyl or ethynyl linkers: synthesis, duplex stability, and fluorescence changes generated by the DNA-dye connector
dc.typejournal article
dc.identifier.doi10.1016/j.tet.2013.11.048
dc.identifier.isiISI:000330816000032
dc.description.volume70
dc.description.issue2
dc.description.startpage380
dc.description.endpage391
dc.publisher.placeTHE BOULEVARD, LANGFORD LANE, KIDLINGTON, OXFORD OX5 1GB, ENGLAND
dcterms.isPartOf.abbreviationTetrahedron
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