Evaluation of Transiently O-6 Protected Guanosine Morpholino Nucleosides in PMO Synthesis

IF 1.7 4区 化学 Q3 CHEMISTRY, ORGANIC
Synlett Pub Date : 2024-05-08 DOI:10.1055/a-2322-3741
Md Qasim, Atanu Ghosh, Arnab Das, Surajit Sinha
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引用次数: 0

Abstract

Here we present a novel strategy to synthesize O-6 protected morpholino guanosine monomers by trimethylsilylethyl group, 1-(4-azido-phenyl) ethan-1-ol and para methoxy benzyl alcohol, respectively. The introduction of this protecting group increases the solubility of the morpholino nucleoside which is crucial during PMO synthesis. HPLC analysis shows trimethylsilylethyl protected monomer gives better coupling efficiency in PMO synthesis compared to regular one. Moreover the nonpolar nature of the O-6 protected monomer facilitated the guanosine rich PMO block in solution.

Abstract Image

在 PMO 合成中对瞬时 O-6 保护的鸟苷吗啉核苷的评估
在这里,我们提出了一种新策略,分别用三甲基硅乙基、1-(4-叠氮苯基)乙醇和对甲氧基苄醇合成 O-6 保护的吗啉鸟苷单体。这种保护基团的引入增加了吗啉核苷的溶解度,这在 PMO 合成过程中至关重要。HPLC 分析表明,与普通单体相比,三甲基硅乙基保护单体在 PMO 合成中具有更好的偶联效率。此外,O-6 保护单体的非极性有助于在溶液中形成富含鸟苷的 PMO 嵌段。
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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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