赖氨酸辅助酯和酰胺甲醇解对核苷的脱保护作用

IF 1.8 3区化学 Q3 CHEMISTRY, ORGANIC

Synthetic Communications Pub Date : 2025-01-31 DOI:10.1080/00397911.2025.2456103

Jyothi Dhuguru , Brandon English , Ryan W. Dellinger , Marie E. Migaud

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引用次数: 0

摘要

基于赖氨酸辅助的核苷衍生酯和芳基酰胺的甲醇分解，建立了一种去酰化方法。本方法补充了已建立的去酰化方法，使用赖氨酸和甲醇的最小摩尔当量在温和加热下产生去酰化核苷和可回收赖氨酸和挥发性甲酯作为副产物。各种酰基化的典型核苷和水解不稳定的非典型核苷，如烟酰胺核苷（NR）及其还原形式（NRH）在赖氨酸辅助条件下被去保护，证明了这种方法的多功能性。在测定了这种一锅法的e因子和反应质量指数后，我们发现这种方法比更成熟的脱酰基化方法更环保。

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Deprotection of nucleosides by lysine-assisted methanolysis of esters and amides

A deacylation method was developed based on lysine-assisted methanolysis of nucleoside-derived esters and arylamides. The present methodology complements well-established deacylation methods, using a minimum molar equivalency of lysine and methanol under mild heating to generate the deacylated nucleoside and recyclable lysine and volatile methyl esters as byproducts. A variety of acylated canonical nucleosides and hydrolytically labile non-canonical nucleosides like nicotinamide riboside (NR) and its reduced form (NRH) were deprotected under such lysine-assisted conditions, demonstrating the versatility of this approach. Having determined this one-pot process’s E-factor and reaction mass index, we find this method greener than the more established deacylation processes.

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来源期刊

Synthetic Communications 化学-有机化学

CiteScore

4.40

自引率

4.80%

发文量

156

审稿时长

4.3 months

期刊介绍： Synthetic Communications presents communications describing new methods, reagents, and other synthetic work pertaining to organic chemistry with sufficient experimental detail to permit reported reactions to be repeated by a chemist reasonably skilled in the art. In addition, the Journal features short, focused review articles discussing topics within its remit of synthetic organic chemistry.