Tomoko Fujino

Triazole-Linked Analogue of Deoxyribonucleic Acid (TLDNA): Design, Synthesis, and Double-Strand Formation with Natural DNA

A new triazole-linked analogue of DNA ((TL)DNA) has been designed and synthesized using click chemistry. The chain elongation reaction using copper-catalyzed Huisgen cycloaddition was successful and gave the artificial oligonucleotide that formed a stable double strand with the complementary strand of natural DNA.

Post-Modification of Triazole-Linked Analogues of DNA for Positively Charged Variants

Table of

Diels–Alder Reaction of Cyclopentadienone Acetal with Pyrrole and Indole

Diels–Alder reactions of a cyclopentadienone acetal with aromatic heterocycles, such as pyrrole or indole, took place with the latter acting as a 2π dienophile. The reaction gave a polycyclic heter...Diels-Alder reactions of a cyclopentadienone acetal with aromatic heterocycles, such as pyrrole or indole, took place with the latter acting as a 2π dienophile. The reaction gave a polycyclic heterocycle in good yield regioselectively. Analysis of the frontier molecular orbitals showed that inverse electron demand interactions control the regioselectivity.

Chimeric RNA Oligonucleotides with Triazole and Phosphate Linkages: Synthesis and RNA Interference.

Chimeric RNA oligonucleotides with an artificial triazole linker were synthesized using solution-phase click chemistry and solid-phase automated synthesis. Scalable synthesis methods for jointing units for the chimeric structure have been developed, and after click-coupling of the jointing units with triazole linkers, a series of chimeric oligonucleotides was prepared by utilizing the well-established phosphoramidite method for the elongation. The series of chimeric 21-mer oligonucleotides that possessed the triazole linker at different strands and positions allowed for a screening study of the RNA interference to clarify the preference of the triazole modifications in small-interfering RNA molecules.