The Impact of Secondary Structure on the Base‐Filling of N‐Methoxy‐1,3‐Oxazinane (MOANA) and N‐Methoxy‐1,3‐Oxazolidine Glycol Nucleic Acid (MOGNA) Oligonucleotides

ChemBioChem, Год журнала: 2024, Номер 26(1)

Опубликована: Сен. 7, 2024

Various single-stranded and hairpin-forming DNA 2'-O-methyl-RNA oligonucleotides bearing a single (2R,3S)-4-(methoxyamino)butane-1,2,3-triol residue esterified from either O1 O2 or O3 were synthesized. Incubation of these with equimolar mixtures formylmethyl derivatives the canonical nucleobases 2-methylbenzimidazole under mildly acidic conditions revealed base-filling modified site to be strongly favored by base stacking double-helix, especially an A-type one. In hairpin oligonucleotides, nucleobase aldehydes followed rules Watson-Crick pairing, thymine being only exception. Hoogsteen strand triple helices, both yield selectivity much more modest.

Язык: Английский

Chemistry of organometallic nucleic acid components: personal perspective and prospects for the future

Dalton Transactions, Год журнала: 2024, Номер unknown

Опубликована: Янв. 1, 2024

Organometallic modifications of biologically important compounds such as drugs, secondary natural products, peptides, and nucleic acids, to name just a few, represent well-established strategy for the development new anticancer antimicrobial agents. Supported by these reasons, over 12 years ago, we initiated research program into organometallic acid components. This account summarizes key results regarding synthetic chemistry biological activities obtained compounds. As chemists, our main goal last has been develop strategies that allow exploration chemical space Accordingly, have developed Michael addition reaction-based methodology enabled synthesis an entirely class glycol (GNA) constituents. Concerning GNA chemistry, also reported first-ever ferrocenyl GNA-RNA "mixed" dinucleoside phosphate analog. Recently, Cu(I)-catalyzed Huisgen azide-alkyne 1,3-dipolar cycloaddition approach novel 1,2,3-triazole-linked ("click") nucleosides. The high value this is because it allows introduction functional (

Язык: Английский

Organomercury oligonucleotide–polydopamine nanoparticle assemblies discriminate between target sequences by Hg(ii)-mediated base pairing

RSC Advances, Год журнала: 2024, Номер 14(51), С. 38279 - 38284

Опубликована: Янв. 1, 2024

An organomercury nucleobase of a hybridization probe can engage in either adsorption on polydopamine nanoparticle or Hg( ii )-mediated base pairing with complementary oligonucleotide. The equilibrium is sensitive to the partner.

Язык: Английский