Crossing the Solubility Rubicon: 15-Crown-5 Facilitates the Preparation of Water-Soluble Sulfo-NHS Esters in Organic Solvents.
Crossing the Solubility Rubicon: 15-Crown-5 Facilitates the Preparation of Water-Soluble Sulfo-NHS Esters in Organic Solvents.
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DOI：
10.1021/acs.bioconjchem.3c00396
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发表时间：
2024-01-17
影响因子：
4.7
通讯作者：
Parkin, Alison
中科院分区：
文献类型：
--
作者：
Yates, Nicholas D. J.;Miles, Connor G.;Spicer, Christopher D.;Fascione, Martin A.;Parkin, Alison
磺胺- nhs酯是一种主要的试剂，促进酰胺键形成之间的羧酸和胺的功能在水中。然而，目前制备磺胺- nhs酯需要先与不溶于有机溶剂的n -羟基磺基琥珀酰亚胺钠盐反应，而疏水羧酸的水溶性较差。因此，相互不相容的溶剂化要求使合成磺酰国民健康保险酯复杂化。作为一种简单、快速、经济的解决方案，我们报道了使用15-冠-5络合n-羟基磺基琥珀酰亚胺钠盐的钠阳离子，使n-羟基磺基琥珀酰亚胺盐可溶于有机溶剂，从而绕过了这些溶剂化不相容问题，从而使酯化反应更清洁，从而提高了活性酯产物的收率。我们还证明，当用于蛋白质胺官能和疏水性羧酸之间的生物偶联反应时，所得的“冠状”磺胺- nhs酯仍然是水溶性的，并且活性不亚于其经典的“无冠”磺胺- nhs对应物。
The Sulfo-NHS ester is a mainstay reagent for facilitating amide bond formation between carboxylic acids and amine functionalities in water. However, the preparation of Sulfo-NHS esters currently requires hydrophobic carboxylic acids, which are poorly water-soluble, to first be reacted with the N-hydroxysulfosuccinimide sodium salt, which is insoluble in organic solvents. The mutually incompatible solvation requirements thus complicate the synthesis of Sulfo-NHS esters. As a simple, rapid, and cost-effective solution to this problem, we report that the use of 15-crown-5 to complex the sodium cation of N-hydroxysulfosuccinimide sodium salt circumnavigates these solvation incompatibility issues by rendering the N-hydroxysulfosuccinimide salt soluble in organic solvents, resulting in a cleaner esterification reaction and thus improved yields of activated ester product. We also demonstrate that the resultant “crowned” Sulfo-NHS-ester remains water-soluble and is no less reactive than its classic “uncrowned” Sulfo-NHS counterpart when used in bioconjugation reactions between protein amine-functionalities and hydrophobic carboxylic acids.
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