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Updated: Aug 2, 2026
15:22
Nucleoside Triphosphates - From Synthesis to Biochemical Characterization
Published on: April 3, 2014
Solid-phase synthesis of oligodeoxyribonucleoside boranophosphates by the boranophosphotriester method
Mamoru Shimizu1, Kazuhiko Saigo, Takeshi Wada
1Department of Medical Genome Sciences, Graduate School of Frontier Sciences, The University of Tokyo, Bioscience Building 702, Kashiwa, Chiba 277-8562, Japan.
The Journal of Organic Chemistry
|May 20, 2006
Summary
Oligodeoxyribonucleoside boranophosphates (BH3-ODNs) were synthesized using a novel solid-phase method. These modified oligonucleotides show significantly enhanced binding affinity to complementary DNA and RNA sequences.
Area of Science:
- Chemical Synthesis
- Oligonucleotide Chemistry
- Biotechnology
Background:
- Oligodeoxyribonucleoside boranophosphates (BH3-ODNs) are modified nucleic acids with potential therapeutic applications.
- Developing efficient synthesis methods for BH3-ODNs is crucial for their further study and application.
Purpose of the Study:
- To develop an optimized solid-phase synthesis method for BH3-ODNs containing all four nucleobases.
- To evaluate the hybridization properties of synthesized BH3-ODNs with complementary DNA and RNA.
Main Methods:
- Solid-phase boranophosphotriester method utilizing 2'-deoxyribonucleoside 3'-boranophosphate monomers with 2-cyanoethyl protecting groups.
- Employing a new condensing reagent and 1,8-bis(N,N-dimethylamino)naphthalene to facilitate efficient condensation.
- Selective deprotection using 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) under anhydrous conditions with terminal acetylation to prevent decomposition.
Main Results:
- Successful synthesis of BH3-ODNs (4mers and 12mers) with all four nucleobases in good yields.
- Thermal denaturing studies demonstrated significantly increased binding affinity of BH3-ODNs to complementary DNA and RNA compared to unmodified oligonucleotides.
- A duplex of d(C(PB)A(PB)G(PB)T)3 and d(ACTG)3 showed a Tm of 44.7°C, and with r(ACUG)3 a Tm of 50.5°C.
Conclusions:
- The developed solid-phase synthesis is effective for producing BH3-ODNs.
- BH3-ODNs exhibit dramatically enhanced binding affinity to complementary DNA and RNA, suggesting their potential as novel nucleic acid therapeutics or diagnostics.
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