4.3 Article

Synthesis of Responsive Fluorescent Nucleobases 7-(Benzofuran-2-yl)-7-deazahypoxanthine and 7-(Benzofuran-2-yl)-7-deazaguanine Using Cross-coupling Reaction

Journal

CHEMISTRY LETTERS
Volume 44, Issue 1, Pages 64-66

Publisher

CHEMICAL SOC JAPAN
DOI: 10.1246/cl.140879

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Funding

  1. Japan Society for the Promotion of Science (JSPS) grant (KAKENHI) [25620126]
  2. JSPS Strategic Young Researcher Overseas Visits Program for Accelerating Brain Circulation program
  3. Grants-in-Aid for Scientific Research [25620126] Funding Source: KAKEN

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In order to develop fluorescent guanine analogs having substitutions at the 7-positions, 7-(benzofuran-2-yl)-7-deazahypoxanthine (la) and 7-(benzofuran-2-yl)-7-deazaguanine (1b), were synthesized from 7-deaza-7-iodohypoxanthine and 7-deaza-7-iodo-2-N-pivaloylguanine via a Suzuki Miyaura cross-coupling, respectively. Compound 1b showed strong fluorescence, with higher fluorescent quantum yields in less polar solvents; meanwhile, la showed higher activity in more polar solvents. It is expected that the guanine analogs can be incorporated into nucleosides to develop new fluorescent oligonucleotides.

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