Expanding Rutinosidase Versatility: Acylated Quercetin Glucopyranosides as Substrates

Kód výsledku v IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F61388971%3A_____%2F24%3A00597615" target="_blank" >RIV/61388971:_____/24:00597615 - isvavai.cz</a>

Nalezeny alternativní kódy

RIV/60076658:12310/24:43908842 RIV/60461373:22330/24:43929140

Výsledek na webu

<a href="https://chemistry-europe.onlinelibrary.wiley.com/doi/10.1002/cctc.202400028" target="_blank" >https://chemistry-europe.onlinelibrary.wiley.com/doi/10.1002/cctc.202400028</a>

DOI - Digital Object Identifier

<a href="http://dx.doi.org/10.1002/cctc.202400028" target="_blank" >10.1002/cctc.202400028</a>

Jazyk výsledku

angličtina

Název v původním jazyce

Expanding Rutinosidase Versatility: Acylated Quercetin Glucopyranosides as Substrates

Popis výsledku v původním jazyce

Rutinosidase is a diglycosidase that catalyzes the cleavage of rutinose (alpha-l-Rhap-(1> 6)-beta-d-Glcp) from rutin or other rutinosides. It is also able to cleave beta-glucopyranosides, e. g., isoquercitrin. This enzyme has a strong transglycosylation activity and a remarkable substrate specificity. We have shown that rutinosidase from Aspergillus niger (AnRut) is able to cleave beta-glucopyranosides acylated at C-6 of glucose (6 '-O-acylisoquercitrin) with acetyl, benzoyl, phenylacetyl, phenylpropanoyl, cinnamoyl, vanillyl, galloyl, 4-hydroxybenzoyl and 3-(4-hydroxy-3-methoxyphenyl)propanoyl. The release of the respective 6-acylglucopyranoses was confirmed by HPLC/MS and NMR methods. Selected compounds, i. e., 6 '-O-acetyl, 6 '-O-benzoyl, and 6 '-O-cinnamyl derivatives of isoquercitrin, were also tested as transglycosylation substrates. Only 6 '-acetylisoquercitrin and 6 '-O-benzoylisoquercitrin underwent transglycosylations by AnRut to produce n-butyl 6-acetyl-beta-d-glucopyranoside and n-butyl 6-benzoyl-beta-d-glucopyranoside. Isoquercitrin 6 '-O-cinnamate yielded on hydrolytic product. Molecular modeling based on the crystal structure of AnRut showed that large aromatic moieties at C-6 ' of isoquercitrin block the side tunnel of AnRut leading into its active site and thus hinder the entry of the acceptor substrate for transglycosylation. This study demonstrates the great substrate flexibility of rutinosidase at the glycone site.

Název v anglickém jazyce

Expanding Rutinosidase Versatility: Acylated Quercetin Glucopyranosides as Substrates

Popis výsledku anglicky

Rutinosidase is a diglycosidase that catalyzes the cleavage of rutinose (alpha-l-Rhap-(1> 6)-beta-d-Glcp) from rutin or other rutinosides. It is also able to cleave beta-glucopyranosides, e. g., isoquercitrin. This enzyme has a strong transglycosylation activity and a remarkable substrate specificity. We have shown that rutinosidase from Aspergillus niger (AnRut) is able to cleave beta-glucopyranosides acylated at C-6 of glucose (6 '-O-acylisoquercitrin) with acetyl, benzoyl, phenylacetyl, phenylpropanoyl, cinnamoyl, vanillyl, galloyl, 4-hydroxybenzoyl and 3-(4-hydroxy-3-methoxyphenyl)propanoyl. The release of the respective 6-acylglucopyranoses was confirmed by HPLC/MS and NMR methods. Selected compounds, i. e., 6 '-O-acetyl, 6 '-O-benzoyl, and 6 '-O-cinnamyl derivatives of isoquercitrin, were also tested as transglycosylation substrates. Only 6 '-acetylisoquercitrin and 6 '-O-benzoylisoquercitrin underwent transglycosylations by AnRut to produce n-butyl 6-acetyl-beta-d-glucopyranoside and n-butyl 6-benzoyl-beta-d-glucopyranoside. Isoquercitrin 6 '-O-cinnamate yielded on hydrolytic product. Molecular modeling based on the crystal structure of AnRut showed that large aromatic moieties at C-6 ' of isoquercitrin block the side tunnel of AnRut leading into its active site and thus hinder the entry of the acceptor substrate for transglycosylation. This study demonstrates the great substrate flexibility of rutinosidase at the glycone site.

Druh

J_imp - Článek v periodiku v databázi Web of Science

CEP obor

—

OECD FORD obor

10608 - Biochemistry and molecular biology

Projekt

Výsledek vznikl pri realizaci vícero projektů. Více informací v záložce Projekty.

Návaznosti

I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace

Rok uplatnění

2024

Kód důvěrnosti údajů

S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

Název periodika

ChemCatChem

ISSN

1867-3880

e-ISSN

1867-3899

Svazek periodika

16

Číslo periodika v rámci svazku

11

Stát vydavatele periodika

US - Spojené státy americké

Počet stran výsledku

7

Strana od-do

e202400028

Kód UT WoS článku

001179319300001

EID výsledku v databázi Scopus

2-s2.0-85186410017