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| 唾液酸衍生物九位羟基的位点选择性磺酸化研究 |
| Site-Selective Sulfonation of the 9-Hydroxyl Group of Sialic Acid Derivatives |
| 投稿时间：2026-04-20 修订日期：2026-05-25 |
| DOI： |
| 中文关键词: 唾液酸 位点选择性 磺酸化 保护基策略 |
| 英文关键词:Sialic acid, Site-selectivity, Sulfonation, Protecting group strategy |
| 基金项目: |
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| 中文摘要: |
| 磺酸化唾液酸在免疫耐受、病原体入侵及肿瘤免疫逃逸中发挥关键作用,其中C9位磺酸化修饰因可作为Siglec受体的精细调控元件而成为研究热点。然而,唾液酸分子内存在多个羟基,使得实现C9位羟基的选择性修饰仍具挑战。本研究以唾液酸为起始原料,通过选择性保护反应活性较高的C2位和C4位羟基,构建了适于C9位选择性修饰的底物骨架。以三氧化硫-吡啶复合物为磺酸化试剂,在四氢呋喃溶剂中、-25℃条件下,实现了C9位羟基的高效、高选择性磺酸化。通过系统优化反应条件与核磁共振波谱表征,确认了目标产物的结构。该策略为9-O-磺酸化唾液酸的简便合成提供了有效途径,为深入探索其生物学功能及开发相关药物奠定了重要的化学基础。 |
| 英文摘要: |
| Sulfated sialic acids play a critical role in immune tolerance, pathogen invasion, and tumor immune evasion. Among these, 9-O-sulfation has become a research hotspot due to its potential function as a fine-tuning element for immunomodulatory Siglec receptors. However, the presence of multiple hydroxyl groups within the sialic acid molecule poses a significant challenge to achieving selective modification of the C9 hydroxyl group. In this study, with sialic acid as the starting material, a suitable substrate skeleton suitable for selective C9 modification was constructed through the regioselective protection of the more reactive hydroxyl groups at the C2 and C4 positions. Efficient and highly selective 9-O-sulfation was then achieved using sulfur trioxide-pyridine complex as the sulfating reagent in tetrahydrofuran at -25 °C. Through systematic optimization of reaction conditions and characterization by nuclear magnetic resonance spectroscopy, the structure of the target product was confirmed. This strategy provides a straightforward and efficient synthetic route to 9-O-sulfated sialic acid, thereby establishing a crucial chemical foundation for in-depth investigations into their biological functions and the development of related therapeutics. |
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