Morpholino-based phosphorothioate analogs via oxathiaphospholane chemistry: synthesis, structural insights and stability

IF 2.7 3区化学 Q1 CHEMISTRY, ORGANIC

Organic & Biomolecular Chemistry Pub Date : 2025-09-04 DOI:10.1039/d5ob01223f

Katarzyna Jastrzębska , Agata Szymańska , Tomasz Pawlak , Rafał Dolot

引用次数: 0

Abstract

We present the application of the oxathiaphospholane method for the synthesis of novel P-stereodefined phosphorothioate N-modified morpholino analogs, showcasing its potential for creating therapeutically relevant compounds. Additionally, we provide valuable structural insights into their stereochemistry, including a detailed analysis of stereochemical configurations. We also report on the enzymatic stability of these compounds in 10% (v/v) fetal bovine serum (FBS), thereby mimicking in vivo conditions. These findings pave the way for further exploration of P-stereodefined nucleic acid analogs in molecular medicine and gene therapy applications.

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通过草硫代磷烷化学的基于morpholino的硫代磷酸酯类似物：合成，结构见解和稳定性。

我们提出应用草酸磷烷方法合成新的p立体定义的磷硫代n修饰的morpholino类似物，展示其创造治疗相关化合物的潜力。此外，我们还提供了有价值的立体化学结构见解，包括立体化学构型的详细分析。我们还报道了这些化合物在10% （v/v）胎牛血清（FBS）中的酶稳定性，从而模拟体内条件。这些发现为进一步探索p立体核酸类似物在分子医学和基因治疗中的应用铺平了道路。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

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来源期刊

Organic & Biomolecular Chemistry 化学-有机化学

CiteScore

5.50

自引率

9.40%

发文量

1056

审稿时长

1.3 months

期刊介绍： Organic & Biomolecular Chemistry is an international journal using integrated research in chemistry-organic chemistry. Founded in 2003 by the Royal Society of Chemistry, the journal is published in Semimonthly issues and has been indexed by SCIE, a leading international database. The journal focuses on the key research and cutting-edge progress in the field of chemistry-organic chemistry, publishes and reports the research results in this field in a timely manner, and is committed to becoming a window and platform for rapid academic exchanges among peers in this field. The journal's impact factor in 2023 is 2.9, and its CiteScore is 5.5.