Solid Supports for the Synthesis of 3′-Aminooxy Deoxy- or Ribo-oligonucleotides and Their 3′-Conjugation by Oxime Ligation - Archive ouverte HAL Accéder directement au contenu
Article Dans Une Revue Journal of Organic Chemistry Année : 2019

Solid Supports for the Synthesis of 3′-Aminooxy Deoxy- or Ribo-oligonucleotides and Their 3′-Conjugation by Oxime Ligation

Résumé

Mono- and triethylene glycol aminooxy derivatives were reacted with levulinic acid, protected with dimethoxytrityl, and immobilized on solid support. The resulting solid supports were used for elongation of oligonucleotides. Then, a mild ammonia treatment was applied to remove the oligonucleotide protecting groups, followed by a treatment with SO mM methoxyamine at pH 4.2, releasing the 3'-aminooxy oligonucleotides by an oxime exchange reaction. The resulting 3'-aminooxy deoxy- or ribo-oligonucleotides were conjugated to various ketones and aldehydes with high efficiency by oxime ligation.
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Dates et versions

hal-02400790 , version 1 (06-11-2020)

Identifiants

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Mathieu Noël, Céline Clément-Blanc, Albert Meyer, Jean-Jacques Vasseur, François Morvan. Solid Supports for the Synthesis of 3′-Aminooxy Deoxy- or Ribo-oligonucleotides and Their 3′-Conjugation by Oxime Ligation. Journal of Organic Chemistry, 2019, 84 (22), pp.14854-14860. ⟨10.1021/acs.joc.9b00848⟩. ⟨hal-02400790⟩
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