在 PMO 合成中对瞬时 O-6 保护的鸟苷吗啉核苷的评估

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

{"title":"在 PMO 合成中对瞬时 O-6 保护的鸟苷吗啉核苷的评估","authors":"Md Qasim, Atanu Ghosh, Arnab Das, Surajit Sinha","doi":"10.1055/a-2322-3741","DOIUrl":null,"url":null,"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.","PeriodicalId":22319,"journal":{"name":"Synlett","volume":null,"pages":null},"PeriodicalIF":1.7000,"publicationDate":"2024-05-08","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Evaluation of Transiently O-6 Protected Guanosine Morpholino Nucleosides in PMO Synthesis\",\"authors\":\"Md Qasim, Atanu Ghosh, Arnab Das, Surajit Sinha\",\"doi\":\"10.1055/a-2322-3741\",\"DOIUrl\":null,\"url\":null,\"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.\",\"PeriodicalId\":22319,\"journal\":{\"name\":\"Synlett\",\"volume\":null,\"pages\":null},\"PeriodicalIF\":1.7000,\"publicationDate\":\"2024-05-08\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Synlett\",\"FirstCategoryId\":\"92\",\"ListUrlMain\":\"https://doi.org/10.1055/a-2322-3741\",\"RegionNum\":4,\"RegionCategory\":\"化学\",\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"Q3\",\"JCRName\":\"CHEMISTRY, ORGANIC\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Synlett","FirstCategoryId":"92","ListUrlMain":"https://doi.org/10.1055/a-2322-3741","RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q3","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}

引用次数: 0

摘要

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。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

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

查看原文本刊更多论文

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

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.

求助全文

通过发布文献求助，成功后即可免费获取论文全文。去求助

来源期刊

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.