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Solid-phase syntheses of oligodeoxyribonucleoside methylphosphonates.

P S Miller, M P Reddy, A Murakami

    Biochemistry
    |September 9, 1986
    PubMed
    Summary
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    Oligodeoxyribonucleoside methylphosphonates (ODMs) of lengths 6-13 are synthesized on polystyrene supports using protected deoxyribonucleosides and methylphosphonic imidazolides. This method offers efficient synthesis and purification of ODMs for potential therapeutic applications.

    Area of Science:

    • * Organic Chemistry
    • * Nucleic Acid Chemistry
    • * Polymer Chemistry

    Background:

    • * Oligodeoxyribonucleoside methylphosphonates (ODMs) are modified oligonucleotides with potential therapeutic applications.
    • * Efficient and reliable synthesis methods are crucial for their development.

    Purpose of the Study:

    • * To develop a robust method for synthesizing ODMs of defined sequences on solid supports.
    • * To optimize reaction conditions for efficient coupling and purification.

    Main Methods:

    • * Synthesis of protected deoxyribonucleoside 3'-(methylphosphonic imidazolides) as intermediates.
    • * Solid-phase synthesis on polystyrene supports using methylphosphonic bis(imidazolide).
    • * Use of tetrazole as an acid catalyst to accelerate condensation reactions.

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    Main Results:

    • * High efficiency (95% completion) and rapid kinetics (5 min half-life for dimer formation) were achieved on polystyrene supports.
    • * Controlled pore glass supports showed lower reaction extents (78%).
    • * A phosphodiester linkage at the 5'-terminus simplified purification and sequence analysis.

    Conclusions:

    • * Polystyrene supports are superior to controlled pore glass for ODM synthesis.
    • * The cyanoethyl phosphoramidite method simplifies deprotection and cleavage from the support.
    • * Affinity chromatography on DEAE-cellulose provides effective purification of the synthesized ODMs.