1997
DOI: 10.1080/07328319708006267
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Oligonucleotide Conjugates Derived from an Electrophilic Site: Conjugation to Baseless Carbohydrate Residue. Synthesis, Hybridization and Modeling Studies

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Cited by 9 publications
(4 citation statements)
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“…Literature precedents indicate that the amine-catalyzed β-elimination of acetate from 8 likely proceeds via iminium ion intermediates ( 9 and 10 , Scheme ). ,,, We and others have used hydride reagents to trap iminium ion intermediates (e.g., 9 ) generated in the reactions of low-molecular-weight amines with AP sites in DNA. , ,, To probe the involvement of iminium ion intermediates in the amine-catalyzed decomposition of 8 , we incubated the AP model compound with piperidine (30 mM) in the presence of the water-compatible hydride reagent NaBH 3 CN (4 equiv) . LC–MS analysis of the resulting reaction mixture revealed that the major peak in the UV and ion current chromatograms displayed an m / z of 484, consistent with the [M + H] + ion of the reduced iminium ion 13 (Scheme , Figure S1).…”
Section: Resultsmentioning
confidence: 99%
“…Literature precedents indicate that the amine-catalyzed β-elimination of acetate from 8 likely proceeds via iminium ion intermediates ( 9 and 10 , Scheme ). ,,, We and others have used hydride reagents to trap iminium ion intermediates (e.g., 9 ) generated in the reactions of low-molecular-weight amines with AP sites in DNA. , ,, To probe the involvement of iminium ion intermediates in the amine-catalyzed decomposition of 8 , we incubated the AP model compound with piperidine (30 mM) in the presence of the water-compatible hydride reagent NaBH 3 CN (4 equiv) . LC–MS analysis of the resulting reaction mixture revealed that the major peak in the UV and ion current chromatograms displayed an m / z of 484, consistent with the [M + H] + ion of the reduced iminium ion 13 (Scheme , Figure S1).…”
Section: Resultsmentioning
confidence: 99%
“…In this process, the reaction of the AP aldehyde with an amine yields an iminium ion intermediate that is selectively reduced by a hydride reagent to yield a chemically stable alkylamine or arylamine attachment to the deoxyribose backbone (Scheme ). , This reaction has been widely employed in mechanistic studies of amine-catalyzed strand cleavage at AP sites in DNA but, perhaps surprisingly, has seen limited use for derivatization or targeted modification of DNA. ,, , In the present studies, reductive amination reactions involving the AP aldehyde residues in DNA were carried out by incubation of AP-containing oligodeoxynucleotides with amine-containing linkers in the presence of the water-compatible hydride reducing agent NaBH 3 CN. , …”
Section: Results and Discussionmentioning
confidence: 99%
“…In the study, 90 the electrophilic centres of oligonucleotides were generated enzymatically: the uracil residues were cut off from the oligonucleotide chain using uracil ± DNA glycosylase to obtain the apurine/apyrimidine fragments. This was followed by modification of the aldehyde-containing oligonucleotides by various ligands carrying an amino group.…”
Section: Synthesis Of Conjugates Using a Carbonyl Derivative Of One O...mentioning
confidence: 99%