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Solid-phase synthesis of oligoribonucleotides.

I Hirao, M Ishikawa, K Miura

    Nucleic Acids Symposium Series
    |January 1, 1985
    PubMed
    Summary

    Researchers developed a new method for synthesizing RNA fragments. This selective deprotection technique allows for efficient 5

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    Area of Science:

    • Organic Chemistry
    • Biochemistry
    • Nucleic Acid Chemistry

    Background:

    • Oligoribonucleotide synthesis requires selective protection and deprotection of hydroxyl groups.
    • The 5'-O-dimethoxytrityl (DMT) group is commonly used for 5'-hydroxyl protection.
    • Efficient and selective deprotection methods are crucial for successful oligonucleotide synthesis.

    Purpose of the Study:

    • To develop a selective deprotection method for the 5'-O-dimethoxytrityl group of oligoribonucleotides.
    • To achieve 5'-deprotection without affecting the 2'-O-tetrahydropyranyl (THP) protecting group.
    • To synthesize specific trinucleotides using an optimized chemical approach.

    Main Methods:

    • Selective deprotection of the 5'-O-DMT group using 1% dichloroacetic acid in dichloromethane at room temperature.
    • Phosphorylation of protected ribonucleosides.
    • Coupling reactions using the bifunctional reagent 2-chlorophenyl-O-O-bis(1-benzotriazolyl) phosphate.
    • Solid-phase synthesis on a polystyrene support.

    Main Results:

    • Successful selective deprotection of the 5'-O-DMT group was achieved without removing the 2'-O-THP group.
    • Phosphorylation and coupling reactions proceeded efficiently.
    • Synthesis of trinucleotides TpTpT, dUpdUpT, and UpUpT was accomplished.

    Conclusions:

    • The described method provides an efficient and selective approach for 5'-O-DMT deprotection in oligoribonucleotide synthesis.
    • This strategy is compatible with other protecting groups, such as 2'-O-THP.
    • The optimized methodology enables the synthesis of specific RNA trinucleotides.

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