使用施陶丁格还原法作为解锁条件合成磷酸二酰胺吗啉寡核苷酸(PMOs)及其在双官能化和三官能化 PMOs 的正交共轭中的用途

IF 1.7 4区 化学 Q3 CHEMISTRY, ORGANIC Synlett Pub Date : 2024-09-11 DOI:10.1055/a-2384-7323
Subhamoy Pratihar, Md Qasim, Surajit Sinha
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引用次数: 0

摘要

利用叠氮芳基氨基甲酸酯保护的氯代磷酰胺单体,成功合成了短磷酰胺吗啉寡核苷酸(PMOs)。使用三苯基膦试剂在中性介质中进行脱保护步骤,可避免使用氯化溶剂。该方法使用了精心定制的树脂支持物、溶剂、解锁剂和偶联试剂组合,以确保高效合成。此外,叠氮芳基氨基甲酸酯保护基团还可作为一种正交保护基团,从而开发出用于生物共轭的双官能和三官能 PMO。这些进展有望拓宽 PMO 在生物医学研究中的潜在应用。
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Synthesis of Phosphorodiamidate Morpholino Oligonucleotides (PMOs) Using Staudinger Reduction as a Deblocking Condition and Its Usefulness for Orthogonal Conjugation in Bi- and Trifunctionalized PMOs

The synthesis of short phosphorodiamidate morpholino oligonucleotides (PMOs) has been successfully achieved using azidoaryl carbamate protected chlorophosphoramidate monomers. The deprotection step carried out in a neutral medium with triphenylphosphine-based reagents avoids the need for chlorinated solvents. This method uses a meticulously tailored combination of resin support, solvents, deblocking agents, and coupling reagents to ensure efficient synthesis. Additionally, the azidoaryl carbamate protecting group has been adapted as an orthogonal protection, enabling the development of bi- and trifunctionalized PMOs for bioconjugation. These advancements are expected to broaden the potential applications of PMOs in biomedical research.

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来源期刊
Synlett
Synlett 化学-有机化学
CiteScore
3.40
自引率
5.00%
发文量
369
审稿时长
1 months
期刊介绍: SYNLETT is an international journal reporting research results and current trends in chemical synthesis in short personalized reviews and preliminary communications. It covers all fields of scientific endeavor that involve organic synthesis, including catalysis, organometallic, medicinal, biological, and photochemistry, but also related disciplines and offers the possibility to publish scientific primary data.
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