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

J 2021

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

KOTIK, M.; K. BRODSKY; P. HALADA; H. JAVURKOVA; H. PELANTOVA et al.

Základní údaje

Originální název

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

Autoři

KOTIK, M.; K. BRODSKY; P. HALADA; H. JAVURKOVA; H. PELANTOVA; D. KONVALINKOVA; P. BOJAROVA a V. KREN

Vydání

CATALYSIS COMMUNICATIONS, 2021, 1566-7367

Další údaje

Jazyk

angličtina

Typ výsledku

Článek v odborném periodiku

Obor

10403 Physical chemistry

Stát vydavatele

Nizozemské království

Utajení

není předmětem státního či obchodního tajemství

Odkazy

URL

Impakt faktor

Impact factor: 3.510

Označené pro přenos do RIV

Ano

Kód RIV

RIV/00216224:90043/21:00139991

Organizační jednotka

CIISB

Klíčová slova anglicky

TransglycosylationRutinosyl azideGlycosidaseActivity rescueRutinGlycoside hydrolase family 5

Štítky

ne MU, rivok

Příznaky

Mezinárodní význam, Recenzováno

Změněno: 5. 5. 2025 11:30, Mgr. Eva Dubská

Anotace

V originále

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.

Návaznosti

90043, velká výzkumná infrastruktura

Název: CIISB

Citovat

KOTIK, M.; K. BRODSKY; P. HALADA; H. JAVURKOVA; H. PELANTOVA; D. KONVALINKOVA; P. BOJAROVA a V. KREN. Access to both anomers of rutinosyl azide using wild-type rutinosidase and its catalytic nucleophile mutant. CATALYSIS COMMUNICATIONS. 2021, roč. 149, JAN, s. 106193-106197. ISSN 1566-7367. Dostupné z: https://doi.org/10.1016/j.catcom.2020.106193.

@article{1846461,
   author = {Kotik, M. and Brodsky, K. and Halada, P. and Javurkova, H. and Pelantova, H. and Konvalinkova, D. and Bojarova, P. and Kren, V.},
   article_number = {JAN},
   doi = {https://doi.org/10.1016/j.catcom.2020.106193},
   keywords = {TransglycosylationRutinosyl azideGlycosidaseActivity rescueRutinGlycoside hydrolase family 5},
   language = {eng},
   issn = {1566-7367},
   journal = {CATALYSIS COMMUNICATIONS},
   title = {Access to both anomers of rutinosyl azide using wild-type rutinosidase and its catalytic nucleophile mutant},
   url = {https://www.sciencedirect.com/science/article/pii/S1566736720302697?via%3Dihub},
   volume = {149},
   year = {2021}
}

TY  - JOUR
ID  - 1846461
AU  - Kotik, M. - Brodsky, K. - Halada, P. - Javurkova, H. - Pelantova, H. - Konvalinkova, D. - Bojarova, P. - Kren, V.
PY  - 2021
TI  - Access to both anomers of rutinosyl azide using wild-type rutinosidase and its catalytic nucleophile mutant
JF  - CATALYSIS COMMUNICATIONS
VL  - 149
IS  - JAN
SP  - 106193
EP  - 106193
SN  - 15667367
KW  - TransglycosylationRutinosyl azideGlycosidaseActivity rescueRutinGlycoside hydrolase family 5
UR  - https://www.sciencedirect.com/science/article/pii/S1566736720302697?via%3Dihub
N2  - 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.
ER  -

KOTIK, M.; K. BRODSKY; P. HALADA; H. JAVURKOVA; H. PELANTOVA; D. KONVALINKOVA; P. BOJAROVA a V. KREN. Access to both anomers of rutinosyl azide using wild-type rutinosidase and its catalytic nucleophile mutant. \textit{CATALYSIS COMMUNICATIONS}. 2021, roč.~149, JAN, s.~106193-106197. ISSN~1566-7367. Dostupné z: https://doi.org/10.1016/j.catcom.2020.106193.

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