Coumarin-based glycosidase substrate compound and synthesis method and application thereof

By designing coumarin-based glycosidase substrate compounds, the problems of poor stability and low synthesis rate of existing chromogenic substrates have been solved, achieving efficient and low-cost chromogenic detection, which is suitable for microbial screening and enzyme activity analysis.

CN122404447APending Publication Date: 2026-07-17JIANGXI SCI & TECH NORMAL UNIV
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Patent Information

Authority / Receiving Office
CN · China
Patent Type
Applications(China)
Current Assignee / Owner
JIANGXI SCI & TECH NORMAL UNIV
Filing Date
2026-03-16
Publication Date
2026-07-17

AI Technical Summary

Technical Problem

Existing aescin enzyme substrates have poor stability, and S-gal® has a low overall synthesis rate, is expensive, and requires a long cultivation time, which limits its widespread application.

Method used

A coumarin-based glycosidase substrate compound with the structure 3,4-cyclohexenyl-7-hydroxy-6-β-D-galactopyranoside coumarin was designed. The structure was well preserved after autoclaving, and the Michaelis constant Km for the reaction with β-galactosidase was low. The synthetic route was simple and suitable for colorimetric detection in solid culture media or gel systems.

Benefits of technology

It improves the stability and synthesis yield of chromogenic products, shortens the culture time, and reduces production costs. It is suitable for microbial screening and enzyme activity localization analysis, and is applicable to the detection of β-galactosidase and similar glycosidases.

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Abstract

本发明属于显色酶底物合成技术领域,公开了一种香豆素基糖苷酶底物化合物及其合成方法与应用。该底物的结构特征在于半乳糖基与3,4‑环己烯基‑6,7‑二羟基香豆素的6位羟基形成β‑糖苷键,其合成方法通过在香豆素母核的7位羟基选择性引入烯丙基作为保护基团,进行糖苷化反应后脱除保护基制得。该合成工艺有效避免了异构体的生成,操作简单,提高了整体反应产率和产物纯度。该底物(S‑Gal)表现出优良的酶解动力学特性,在β‑半乳糖苷酶的作用下水解生成3,4‑环己烯基‑6,7‑二羟基香豆素,该结构能与铁、铝等金属离子螯合形成黑色或黄色沉淀,显著提升了β‑糖苷酶检测的灵敏度与效果。
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Citation Information

Patent Citations

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