新型6-取代丙炔磺酰胺β-环糊精的合成与聚乙二醇化

IF 1.5 4区化学 Q3 CHEMISTRY, ORGANIC

Tetrahedron Letters Pub Date : 2025-04-08 DOI:10.1016/j.tetlet.2025.155592

Thomas K. Green

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引用次数: 0

摘要

以七烷基-2,3- o -二甲基-6- o -磺基丁基-β-CD钠盐为原料，分两步合成了一种新型的单异构体-巯基磺基-β-环糊精（β-CD）。通过铜催化叠氮化物-炔环加成（CuAAC），中间体磺酰胺β-CD与叠氮化物端聚乙二醇（N3-PEG5-OH和N3-PEG47-OCH3）在第三步进行聚乙二醇化。该衍生化策略首次利用了磺基丁醚（SBE）阴离子环糊精的磺酸功能反应性，得到了具有扩展疏水腔的水溶性单异构体peg -三唑-磺酰胺β-CD。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

Synthesis and PEGylation of a novel, per-6-substituted propargyl sulfonamide β-cyclodextrin

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Synthesis and PEGylation of a novel, per-6-substituted propargyl sulfonamide β-cyclodextrin

A novel single isomer, per-6-substituted alkyne-terminated sulfonamide β-cyclodextrin (β-CD) was synthesized, in two steps, from heptakis-2,3-O-dimethyl-6-O-sulfobutyl-β-CD, sodium salt. The intermediate sulfonamide β-CD was then per-6-PEGylated in a third step with azide-terminated polyethylene glycols (N₃-PEG₅-OH and N₃-PEG₄₇-OCH₃) by copper-catalyzed azide-alkyne cycloaddition (CuAAC) The described derivatization strategy is the first to exploit the reactivity of sulfonate functions of sulfobutylether (SBE) anionic cyclodextrins, and results in a water-soluble, single isomer PEG-triazole-sulfonamide β-CD with an extended hydrophobic cavity.

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来源期刊

Tetrahedron Letters 化学-有机化学

CiteScore

3.50

自引率

5.60%

发文量

521

审稿时长

28 days

期刊介绍： Tetrahedron Letters provides maximum dissemination of outstanding developments in organic chemistry. The journal is published weekly and covers developments in techniques, structures, methods and conclusions in experimental and theoretical organic chemistry. Rapid publication of timely and significant research results enables researchers from all over the world to transmit quickly their new contributions to large, international audiences.