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

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 pr...

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Bibliographic Details
Published in:Journal of organic chemistry 2019-11, Vol.84 (22), p.14854-14860
Main Authors: Noël, Mathieu, Clément-Blanc, Céline, Meyer, Albert, Vasseur, Jean-Jacques, Morvan, François
Format: Article
Language:English
Subjects:
Analytical chemistry
Chemical Sciences
Medicinal Chemistry
Organic chemistry
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Summary: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 50 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.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.9b00848