| 柴云龙,刘璐,曹鸿志.α-淀粉酶检测剂EPS-G7关键前体pNP-α-AcG7的合成[J].中国海洋药物,2027,(3):-. |
| α-淀粉酶检测剂EPS-G7关键前体pNP-α-AcG7的合成 |
| Chemical Synthesis of pNP-α-AcG7, a Key Precursor of EPS?G7 for α?Amylase Assay |
| 投稿时间：2026-03-24 修订日期：2026-04-14 |
| DOI： |
| 中文关键词: O-芳基糖苷 α选择性糖苷化 寡糖合成 EPS-G7 |
| English Keywords:O-aryl glycoside α-selective glycosylation oligosaccharides synthesis |
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| 中文摘要: |
| 目的 本研究旨在发展并运用芳香亲核取代(SNAr)途径介导的高立体选择性α-O-芳基糖苷化反应,合成α-淀粉酶检测试剂EPS-G7的关键前体pNP-α-AcG7。方法 选取具有与目标七糖结构相似的麦芽二糖作为模型底物,系统考察了不同碱性体系、添加剂及温度对该SNAr介导α-O-芳基糖苷化反应的产率及α-选择性的影响,筛选出最优反应条件。在此基础上,以廉价β-环糊精为起始原料,经乙酰解开环及选择性脱除还原端异头位乙酰基得到麦芽七糖半缩醛,并使用优化后的α-O-芳基糖苷化反应实现目标分子pNP-α-AcG7的合成。结果 模型反应筛选结果表明在DMSO溶剂中,以Cs2CO3(2.2 equiv)为碱并添加18-冠醚-6(4.4 equiv)的室温体系表现出最佳反应活性,以63%的产率和良好的α-立体选择性(α/β > 86 : 14)获得α-O-芳基糖苷化产物。以该反应作为关键步骤,三步38%总产率成功实现了pNP-α-AcG7的化学合成。结论 本研究进一步优化了SNAr介导的α-O-芳基糖苷化反应体系,为相应糖苷分子的合成提供了新途径,并实现了EPS-G7关键前体pNP-α-AcG7的有效合成。 |
| English Summary: |
| Objective This study aims to develop and apply a highly stereoselective nucleophilic aromatic substitution (SNAr) α-O-aryl glycosylation approach for the synthesis of pNP-α-AcG7, a key precursor of EPS-G7 for α-amylase assay in clinical test. Methods Maltose was selected as as the model substrate to investigate the effects of different base systems, additives, and temperature on the yield and α-selectivity of the SNAr-mediated α-O-aryl glycosylation, allowing for the identification of optimal reaction conditions. Subsequently, inexpensive β-cyclodextrin was used as the starting material, which was subjected to acetolysis and selective removal of the anomeric acetyl group at the reducing end to obtain the maltose heptaose hemiacetal. The target molecule pNP-α-AcG7 was then synthesized using the optimized α-O-aryl glycosylation reaction. Results The model reaction screening revealed that the optimal conditions using Cs2CO3 (2.2 equiv) as the base and 18-crown-6 (4.4 equiv) as an additive in DMSO at room temperature. These condition afforded the α-O-aryl glycosylation product in 63% yield with good α-stereoselectivity (α/β > 86 : 14). Employing this reaction as the key step, pNP-α-AcG7 was successfully synthesized in three steps with an overall 38% yield. Conclusion The optimized SNAr-mediated α-O-aryl glycosylation reaction provides a novel approach for the synthesis of the synthesis of pNP-α-AcG7, a key precursor of EPS-G7. |
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