Oligonucleotides containing 7-Deaza-2 `-deoxyinosine as universal nucleoside: Synthesis of 7-halogenated and 7-alkynylated derivatives, ambiguous base pairing, and dye functionalization by the alkyne - Azide `Click' reaction

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dc.contributor.authorSeela, Frank
dc.contributor.authorMing, Xin
dc.date.accessioned2021-12-23T16:06:29Z-
dc.date.available2021-12-23T16:06:29Z-
dc.date.issued2008
dc.identifier.issn0018019X
dc.identifier.urihttps://osnascholar.ub.uni-osnabrueck.de/handle/unios/7422-
dc.description.abstractOligonucleotides containing 7-deaza-2'-deoxyinosine derivatives bearing 7-halogen substituents or 7-alkynyl groups were prepared. For this, the phosphoramidites 2b-2g containing 7-substituted 7-deaza-T-deoxyinosine analogues 1b-1g were synthesized (Scheme2). Hybridization experiments with modified oligonucleotides demonstrate that all 2'-deoxyinosine derivatives show ambiguous base pairing, as 2'-deoxyinosine does. The duplex stability decreases in the order C(d) > A(d) > T(d) > G(d) when 2b-2g pair with these canonical nucleosides (Table 6). The self-complementary duplexes 5'-d(F(7)c(7)I-C)(6),. d(Br(7)c(7)I-C)(6), and d(I(7)C(7)I-C)(6) are more stable than the parent duplex d (C(7)I-C)(6) (Table 7). All oligonucleotide containing the octa-1,7-diyn-1-yl derivative 1g, i.e., 27, was functionalized with the nonfluorescent 3-azido-7-hydroxycoumarin (28) by the Huisgen - Sharpless - Meldal cycloaddition `click' reaction to afford the highly fluorescent oligonucleotide conjugate 29 (Scheme 3). Consequently oligonucleotides incorporating the derivative 1g bearing a terminal C C bond show a number of favorable properties: i) it is possible to activate them by labeling with reporter molecules employing the `click' chemistry. ii) Space demanding residues introduced in the 7-position of the 7-deazapurine base does not interfere with duplex structure and stability (Table 8). iii) The ambiguous pairing character of the nucleobase makes them universal probes for numerous applications in oligonucleotide chemistry, molecular biology, and nanobiotechnology.
dc.language.isoen
dc.publisherWILEY-BLACKWELL
dc.relation.ispartofHELVETICA CHIMICA ACTA
dc.subject2'-DEOXYINOSINE
dc.subject2'-DEOXYTUBERCIDIN
dc.subjectChemistry
dc.subjectChemistry, Multidisciplinary
dc.subjectDEOXYINOSINE
dc.subjectDNA
dc.subjectDUPLEX STABILITY
dc.subjectOLIGOMERS
dc.subjectSIDE-CHAINS
dc.subjectSOLID-PHASE SYNTHESIS
dc.subjectTERMINAL TRIPLE BONDS
dc.titleOligonucleotides containing 7-Deaza-2 `-deoxyinosine as universal nucleoside: Synthesis of 7-halogenated and 7-alkynylated derivatives, ambiguous base pairing, and dye functionalization by the alkyne - Azide `Click' reaction
dc.typejournal article
dc.identifier.doi10.1002/hlca.200890131
dc.identifier.isiISI:000258088800001
dc.description.volume91
dc.description.issue7
dc.description.startpage1181
dc.description.endpage1200
dc.publisher.placeCOMMERCE PLACE, 350 MAIN ST, MALDEN 02148, MA USA
dcterms.isPartOf.abbreviationHelv. Chim. Acta
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