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Solid Supports for the Synthesis of 3'-Aminooxy Deoxy- or Ribo-oligonucleotides and Their 3'-Conjugation by Oxime Ligation.
The Journal of Organic Chemistry ( IF 3.3 ) Pub Date : 2019-10-25 , DOI: 10.1021/acs.joc.9b00848
Mathieu Noël 1 , Céline Clément-Blanc 1 , Albert Meyer 1 , Jean-Jacques Vasseur 1 , François Morvan 1
Affiliation  

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.

中文翻译:

用于合成3'-氨基氧基脱氧或核糖寡核苷酸及其通过肟连接的3'-偶联的固体支持物。

使单乙二醇和三乙二醇氨基氧基衍生物与乙酰丙酸反应,用二甲氧基三苯甲基保护,并固定在固体支持物上。所得的固体支持物用于寡核苷酸的延伸。然后,进行温和的氨处理以除去寡核苷酸保护基,然后用50mM的pH 4.2的甲氧基胺处理,通过肟交换反应释放3'-氨基氧基寡核苷酸。通过肟连接,将所得的3'-氨氧基脱氧或核糖寡核苷酸与各种酮和醛高效地偶联。
更新日期:2019-10-25
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