Access to both anomers of rutinosyl azide using wild-type rutinosidase and its catalytic nucleophile mutant

0541617 - MBÚ 2022 RIV NL eng J - Journal Article
Kotík, Michael - Brodsky, Katerina - Halada, Petr - Javůrková, Hana - Pelantová, Helena - Konvalinková, Dorota - Bojarová, Pavla - Křen, Vladimír
Access to both anomers of rutinosyl azide using wild-type rutinosidase and its catalytic nucleophile mutant.
Catalysis Communication. Roč. 149, JAN 15 (2021), č. článku 106193. ISSN 1566-7367. E-ISSN 1873-3905
R&D Projects: GA ČR(CZ) GA19-00091S; GA MŠMT(CZ) LTC20069
Research Infrastructure: CIISB - 90043
Institutional support: RVO:61388971
Keywords : Transglycosylation * Rutinosyl azide * Glycosidase * Activity rescue * Rutin * Glycoside hydrolase family 5
OECD category: Biochemistry and molecular biology
Impact factor: 3.510, year: 2021
Method of publishing: Open access
https://www.sciencedirect.com/science/article/pii/S1566736720302697

Rutinosidases hydrolyze beta-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 alpha-azide. On the other hand, rutinosyl beta-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.
Permanent Link: http://hdl.handle.net/11104/0319150