2013 Fiscal Year Final Research Report
Development of artificial aromatic nucleic acid with cell membrane permeability
| Project/Area Number |
24659045
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| Research Category |
Grant-in-Aid for Challenging Exploratory Research
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| Allocation Type | Single-year Grants |
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| Research Field |
Drug development chemistry
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| Research Institution | Gifu University |
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Principal Investigator |
UENO Yoshihito 岐阜大学, 応用生物科学部, 教授 (20250467)
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| Project Period (FY) |
2012-04-01 – 2014-03-31
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| Keywords | アンチセンス核酸 / 細胞膜透過性 / ヌクレアーゼ耐性 / RNA親和性 / DNA二重鎖 / RNA二重鎖 / 熱力的安定性 / 熱力学的安定性 |
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| Research Abstract |
The purpose of this study is development of artificial aromatic nucleic acid with cell membrane permeability which involves a benzene ring instead of a ribose ring. (S)-mandelic acid was used as a starting material. After esterification, iodization, reduction, and silylation, it was converted to a boronic acid derivative. Coupling reaction of it with an adenine or cytosine in the presence of cupper (II) produced adenine and cytosine analogs in good yields. It was found that the analogs reduced thermal stabilities of DNA/DNA and DNA/RNA duplexes, but the analogs possessed high base discrimination abilities.
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