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Access to both anomers of rutinosyl azide using wild-type rutinosidase and its catalytic nucleophile mutant
Catalysis Communications ( IF 3.7 ) Pub Date : 2020-10-10 , DOI: 10.1016/j.catcom.2020.106193
Michael Kotik , Katerina Brodsky , Petr Halada , Hana Javůrková , Helena Pelantová , Dorota Konvalinková , Pavla Bojarová , Vladimír Křen

Rutinosidases hydrolyze β-rutinosylated flavonoids. As retaining glycosidases they also have a transglycosylation activity. Here we show that two newly identified wild-type rutinosidases, which are members of the glycoside hydrolase family 5–23, are capable of glycosylation of an inorganic azide with rutin as a glycosyl donor, yielding rutinosyl β-azide. On the other hand, rutinosyl α-azide was synthesized by the catalytic nucleophile mutant of the rutinosidase from Aspergillus niger, which also belongs to GH5–23. Thus, we were able to synthesize at a preparatory scale both anomers of rutinosyl azide from rutin using either wild-type or mutant rutinosidases of GH5–23.



中文翻译:

使用野生型芸香糖苷酶及其催化亲核突变体获得芸香苷叠氮化物的两种异构体

芸香糖苷酶水解β-芸香糖基化的类黄酮。作为保留的糖苷酶,它们还具有转糖基化活性。在这里,我们显示了两个新近鉴定的野生型芸香糖苷酶,它们是5-23糖苷水解酶家族的成员,能够将无机叠氮化物与芦丁作为糖基供体进行糖基化,产生芸香糖基β-叠氮化物。另一方面,芸苔苷α-叠氮化物是由黑曲霉的芸苔苷酶的催化亲核突变体合成的,它也属于GH5-23。因此,我们能够使用GH5-23的野生型或突变型芸香糖苷酶,从芦丁中合成芦丁酰化叠氮糖苷的两个异构体。

更新日期:2020-10-17
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