Synthesis of Nucleoside Derivatives of N-Acetyl-7-nitroindoline, Their Incorporation into the DNA Oligomer, and Evaluation of Their Photoreactivity in the DNA/RNA Duplex

Kenji Kikuta, Jan Barta, Yosuke Taniguchi, Shigeki Sasaki

Research output: Contribution to journalArticlepeer-review

Abstract

N-Acetyl-7-nitroindoline has a characteristic reaction in that its acetyl group is photo-activated to acetylate amines to form amides. In this study, the N-acetyl-7-nitroindoline part was connected to the 2′-deoxyri-bose part at the 3- or 5-position or to a glycerol unit at the 3-position through an ethylene linker (1, 2, and 3, respectively). They were incorporated into the oligodeoxynucleotides, and their photo-reactivities toward the complementary RNA were evaluated. The acetyl group of 1 was photo-activated to form the deacelylated nitroso derivative without affecting the RNA strand. The photoreaction with 2 suggested acetylation of the RNA strand. In contrast, compound 3 formed the photo-cross-linked adduct with the RNA. These results have shown the potential application of N-acetyl-7-nitroindoline unit in aqueous solutions.

Original languageEnglish
Pages (from-to)1210-1219
Number of pages10
JournalChemical and Pharmaceutical Bulletin
Volume68
Issue number12
DOIs
Publication statusPublished - Dec 1 2020

All Science Journal Classification (ASJC) codes

  • Chemistry(all)
  • Drug Discovery

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