| 肖文丽,张家彬.化学通报,2026,89(6):737-742. |
| 尿苷二磷酸-6-脱氧-6-叠氮-α-D-吡喃半乳糖的化学酶法合成研究 |
| Study on the Chemoenzymatic Synthesis of UDP-α-6-N3-Galactose |
| 投稿时间：2026-03-05 修订日期：2026-04-02 |
| DOI： |
| 中文关键词: UDP-α-6-N3-Galactose 化学酶法合成 叠氮 |
| 英文关键词:UDP-α-6-N3-Galactose, Chemical-enzymatic synthesis, Azide. |
| 基金项目: |
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| 摘要点击次数: 26 |
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| 中文摘要: |
| 尿苷二磷酸-6-脱氧-6-叠氮-α-D-吡喃半乳糖（UDP-α-6-N3-Galactose）是一种重要的糖核苷酸类似物，可作为生物正交反应的化学把手，在糖生物学研究中具有广泛应用价值。本研究开发了一条高效的化学酶法合成路线，以α-1-O-苄基半乳糖为起始原料，经氧化步骤高选择性地构建α-1-磷酸半乳糖衍生物。该方法有效避免了传统糖-1-磷酸合成中易于发生的异构化或构型翻转问题。再将该衍生物直接应用于UDP 糖焦磷酸化酶(AtUSP)催化酶促偶联反应。该化学酶法路线将化学合成的灵活性与酶促反应的高效性和立体选择性相结合，操作简便，以31%的总产率获得目标产物，为含叠氮官能团的不稳定糖核苷酸提供了可靠的制备途径，也为后续基于点击化学的糖基化机制研究及糖链标记示踪奠定了物质基础。 |
| 英文摘要: |
| Uridine diphosphate-6-deoxy-6-azido-α-D-galactose(UDP-α-6-N3-Galactose) is an important glycoside nucleotide analog, which can be used as a chemical handle for bioorthogonal reactions, and has extensive application value in glycobiology research. In this study, an efficient chemical-enzymatic synthesis route was developed, starting from α-1-O-benzyl galactose, and α-1-phosphoryl galactose derivatives were constructed with high selectivity through an oxidation step. This method effectively avoids the problems of isomerization or configuration inversion that are prone to occur in the traditional synthesis of sugar-1-phosphate. We then directly applied the derivative to the enzymatic coupled reaction catalyzed by UDP-sugar pyrophosphorylase. This chemical-enzymatic route combines the flexibility of chemical synthesis with efficiency and stereoselectivity of enzymatic reactions, featuring simple operation and yielding the targe product in 31% overall yield. It provides a reliable preparation pathway for unstable glycoside nucleotides containing azide functional groups and lays a material foundation for the subsequent study of glycosylation mechanisms based on click chemistry and the labeling and tracing of glycan chains. |
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