Functionalized Silver-Ion-Mediated -dC/-dC Hybrid Base Pairs with Exceptional Stability: -d-5-Iodo-2-Deoxycytidine and Its Octadiynyl Derivative in Metal DNA

DC FieldValueLanguage
dc.contributor.authorMueller, Sebastian Lars
dc.contributor.authorZhou, Xinglong
dc.contributor.authorLeonard, Peter
dc.contributor.authorKorzhenko, Oxana
dc.contributor.authorDaniliuc, Constantin
dc.contributor.authorSeela, Frank
dc.date.accessioned2021-12-23T16:13:22Z-
dc.date.available2021-12-23T16:13:22Z-
dc.date.issued2019
dc.identifier.issn09476539
dc.identifier.urihttps://osnascholar.ub.uni-osnabrueck.de/handle/unios/10537-
dc.description.abstractSilver-mediated -dC-Ag+--dC hybrid base pairs decorated with 5-iodo- or 5-octadiynyl residues are well accommodated in duplex DNA. A strong T-m increase and favorable thermodynamic data for duplex DNA were observed after addition of silver ions. The phenomenon is particularly obvious when both nucleobases of the base pairs are functionalized. Neither the position of the base pair, nor the type of 5-substituent had a negative influence. On the contrary, functionalization of conventional silver-mediated -dC-Ag+--dC homo base pairs showed a negative impact induced by the bulky substituents. To this end, cytosine modified 12-mer oligodeoxynucleotides were prepared by solid-phase synthesis employing new -anomeric 2-deoxycytidine phosphoramidites. A multigram scale synthesis was developed for 5-iodo--d-2-deoxycytidine (1) employing the direct glycosylation of cytosine with Hoffer's -d-halogenose followed by separation of anomeric DMT nucleosides. Regarding base-pair stability and functionalization silver-mediated /-dC hybrid base pairs were found to be superior to /-dC homo pairs. According to their extraordinary properties, they might find applications in DNA diagnostics, material science, or nanotechnology.
dc.language.isoen
dc.publisherWILEY-V C H VERLAG GMBH
dc.relation.ispartofCHEMISTRY-A EUROPEAN JOURNAL
dc.subjectALPHA-OLIGODEOXYNUCLEOTIDES
dc.subjectanomeric hybrid base pairs
dc.subjectBINDING
dc.subjectChemistry
dc.subjectChemistry, Multidisciplinary
dc.subjectCRYSTAL-STRUCTURE
dc.subjectCYTOSINE
dc.subjectDNA
dc.subjectDUPLEX STABILITY
dc.subjectENHANCED STABILITY
dc.subjectGLYCOSYLATION
dc.subjectIMPACT
dc.subjectNUCLEIC-ACID
dc.subjectnucleosides
dc.subjectPARALLEL
dc.subjectsilver
dc.subjectX-ray structure
dc.titleFunctionalized Silver-Ion-Mediated -dC/-dC Hybrid Base Pairs with Exceptional Stability: -d-5-Iodo-2-Deoxycytidine and Its Octadiynyl Derivative in Metal DNA
dc.typejournal article
dc.identifier.doi10.1002/chem.201805299
dc.identifier.isiISI:000460678500024
dc.description.volume25
dc.description.issue12
dc.description.startpage3077
dc.description.endpage3090
dc.contributor.orcid0000-0002-6709-3673
dc.contributor.researcheridB-5073-2011
dc.identifier.eissn15213765
dc.publisher.placePOSTFACH 101161, 69451 WEINHEIM, GERMANY
dcterms.isPartOf.abbreviationChem.-Eur. J.
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