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作为基质工程前体的N-Difluoroacetylhexosamine用于糖化反应

Ya-Lin Cao¹, Jian-Qun Deng¹, Yi Li¹

¹Key Laboratory of Chemical Biology of Natural Products (Ministry of Education), School of Pharmaceutical Sciences, Cheeloo College of Medicine, Shandong University, Jinan, Shandong 250012, People's Republic of China.

Organic letters

|September 4, 2024

概括

我们开发了一种使用N-difluoroacetylglucosamine (GlcNDFA) 合成复杂寡糖的新化学策略. 这种方法有效地产生了德卡巴林,一种类似于肝素的药物,展示了GlcNDFAFA.

科学领域:

碳水化合物化学碳水化合物化学
化学生物学化学生物学
药用化学医学化学

背景情况:

橄糖化合物合成对于开发治疗药物和理解生物过程至关重要.
常规的葡萄糖胺保护组可以在合成途径中限制基质的兼容性和稳定性.
开发高效,强大的合成结构定义多糖的方法仍然是一个挑战.

研究的目的:

引入和评估N-difluoroacetylglucosamine (GlcNDFA) 作为一个新型的前体在寡糖化合物合成.
评估GlcNDFA与N-trifluoroacetylglucosamine等常规保护组相比的优势.
证明GlcNDFA在复杂,生物相关多糖的多步合成中的应用.

主要方法:

开发一种化学进化策略,使用 GlcNDFA 进行寡糖组装.
对 GlcNDFA 和 N-trifluoroacetylglucosamine 进行基质兼容性和稳定性的比较分析.
建立了一个16步合成途径,使用GlcNDFA.FA生产dekaparin.

主要成果:

与N-trifluoroacetylglucosamine相比,GlcNDFA证明了基质与糖转移酶的增强兼容性.
GlcNDFA在水性环境中表现出更好的稳定性,使其在合成过程中更容易使用.
16个步骤的合成产生了同质的德卡巴林,一种类似于肝素的药物,其显着的产量为62.2%.

结论:

N-difluoroacetylglucosamine (GlcNDFA) 是一种高效的前体,用于合成寡糖的化学进化策略.
GlcNDFA的优越性质使复杂的,结构定义的多糖化合物能够精确有效地构建.
这种方法对于可扩展的治疗性多糖类 (如德卡帕林) 的生产具有重大潜力.

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