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Transglycosylation toward naringenin-7-O-glucoside using an N180H mutant of Coprinopsis cinerea endo-β-N-acetylglucosaminidase.
Biochemical and Biophysical Research Communications ( IF 2.5 ) Pub Date : 2020-07-31 , DOI: 10.1016/j.bbrc.2020.06.128
Takao Ohashi 1 , Yu Fujisawa 1 , Marc R Hayes 2 , Ryo Misaki 1 , Jörg Pietruszka 3 , Kazuhito Fujiyama 1
Affiliation  

Flavonoids are generally glycosylated, and the glycan moieties of flavonoid glycosides are known to greatly affect their physicochemical and biological properties. Thus, the development of a variety of tools for glycan remodeling of flavonoid glycosides is highly desired. An endo-β-N-acetylglucosaminidase mutant Endo-CC N180H, which is developed as an excellent chemoenzymatic tool for creating sialylglycoproteins, was employed for the glycosylation of flavonoids. Endo-CC N180H transferred the sialyl biantennary glycans from the sialylglyco peptide to pNP-GlcNAc and narigenin-7-O-glucoside. The kinetic parameters of Endo-CC N180H towards SGP and pNP-GlcNAc were determined. Flavonoid glucosides harboring a 1,3-diol structure in the glucose moieties acted as substrates of Endo-CC N180H. We proposed that the sialyl biantennary glycan transfer to the flavonoid by Endo-CC N180H could pave the way for the improvement of the inherent biological functions of the flavonoids and creation of novel flavonoid glycoside derivatives for future human health benefits including foods and drugs.



中文翻译:

使用灰葡萄孢菌内切-β-N-乙酰氨基葡糖苷酶的N180H突变体对柚皮素-7-O-葡萄糖苷进行转糖基化。

类黄酮通常是糖基化的,已知类黄酮糖苷的聚糖部分会极大地影响其理化和生物学特性。因此,迫切需要开发用于黄酮类糖苷的聚糖重塑的多种工具。将内切-β - N-乙酰氨基葡糖苷酶突变体Endo-CC N180H开发为用于创建唾液酸糖蛋白的优秀化学酶工具,用于将类黄酮糖基化。Endo-CC N180H将唾液酸双触角聚糖从唾液酸糖肽转移到p NP-GlcNAc和成栗素-7- O-葡萄糖苷。Endo-CC N180H对SGP和p的动力学参数确定了NP-GlcNAc。在葡萄糖部分中具有1,3-二醇结构的类黄酮糖苷充当Endo-CC N180H的底物。我们认为,通过Endo-CC N180H将唾液酸双触角聚糖转移到类黄酮上,可以为改善类黄酮的固有生物学功能和创造新型类黄酮糖苷衍生物(包括食品和药品)对人类未来的健康发展铺平道路。

更新日期:2020-07-31
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