| 曹爽,仲侃,李春霞.a2,6连接的氟代唾液酸寡糖的化学酶法合成[J].中国海洋药物,2025,(5):-. |
| a2,6连接的氟代唾液酸寡糖的化学酶法合成 |
| Chemoenzymatic synthesis of a2,6 linked fluorosialic acid oligosaccharides |
| 投稿时间：2024-03-22 修订日期：2024-08-03 |
| DOI： |
| 中文关键词: 氟代唾液酸 化学酶法合成 缩醛酶 |
| English Keywords:fluorosialic acid chemoenzymatic synthesis acetalase |
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| 中文摘要: |
| 目的 利用化学酶法合成策略合成系列a2,6连接C9位氟取代的唾液酸化poly-LacNAc糖链。方法 利用化学合成得到C6位氟代ManNAc单糖9,再以化合物9为供体,三种不同聚合度的底物LacNAcbproN3, diLacNAcbproN3, triLacNAcbproN3为受体,在缩醛酶aldolase、CMP唾液酸合成酶NmCSS以及a2,6唾液酸转移酶Pd2,6ST(mutant)的催化下得到目标化合物1, 2, 3。结论 通过化学酶法合成策略,高效的合成了a2,6连接的9位氟代唾液酸化poly-LacNAc寡糖1, 2, 3,证明了使用的细菌来源的酶有广泛的底物适应性,可以识别6位或9位氟代衍生化的糖,为后续其他氟代唾液酸寡糖的制备及其功能研究提供基础。 |
| English Summary: |
| Objective Synthesis of a series of a2,6-linked C9-fluorinated sialylated poly-LacNAc with chemoenzymatic synthetic strategy. Methods The C6-fluorinated ManNAc (compound 9) was obtained by chemical synthesis, and then the target compounds were obtained under the catalysis of aldolase (E. coli), NmCSS (Neisseria meningitides), Pd2,6ST (Photobacterium damselae) with compound 9 as donor and three glycans, LacNAcbproN3, diLacNAcbproN3, triLacNAcbproN3 as acceptors. Conclusion Using enzymatic synthesis strategy, we efficiently synthesized 9-fluorinated a2,6-linked poly-LacNAc oligosaccharides 1, 2, and 3, demonstrating the ability of the relevant enzymes of bacterium with promiscuous substrate specificities can recognize sialic acid derivatized with fluorine at positions 6 or 9. This lays the foundation for further studies on the preparation and functions of other fluorinated sialyloligosaccharides. |
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