Biocatalyzed Reactions towards Functional Food Components 4-Alkylcatechols and Their Analogues

Result code in IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F61388971%3A_____%2F20%3A00534585" target="_blank" >RIV/61388971:_____/20:00534585 - isvavai.cz</a>

Result on the web

<a href="https://www.mdpi.com/2073-4344/10/9/1077" target="_blank" >https://www.mdpi.com/2073-4344/10/9/1077</a>

DOI - Digital Object Identifier

<a href="http://dx.doi.org/10.3390/catal10091077" target="_blank" >10.3390/catal10091077</a>

Result language

angličtina

Original language name

Biocatalyzed Reactions towards Functional Food Components 4-Alkylcatechols and Their Analogues

Original language description

Catechols are antioxidants and radical scavengers with a broad medical potential. 4-Methylcatechol (1b) and 4-ethylcatechol (2b) (occurring in some traditional fermented and smoked foods) activate the cell defense against oxidative stress. We examined the biocatalyzed reactions towards 4-n-alkylcatechols with different side chains length, which is a factor important for the biological activities of catechols. 4-n-Alkylcatechols with methyl through heptyl side chains (1b-7b) were obtained in one pot by (i) oxidation of phenols 1a-7a with tyrosinase from Agaricus bisporus followed by (ii) reduction of ortho-quinones (intermediates) with L-ascorbic acid sodium salt. The conversions decreased with increasing side chain length. The preparative reactions were carried out with substrates 1a-5a. The isolated yields of the purified products decreased from 59% in 2b to 10% in 5b in correlation with logP of the substrates. Homology modeling indicated that the affinities of two tyrosinase isoforms (PPO3 and PPO4) to the substrates with side chains longer than C2 decreased with increasing side chain length. This was probably due to steric limitations and to missing interactions of the extended side chains in the active sites. We envisage using the model to predict further substrates of tyrosinase and testing the products, catechols, for radical-scavenging and biological activities.

Czech name

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Czech description

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Type

J_imp - Article in a specialist periodical, which is included in the Web of Science database

CEP classification

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OECD FORD branch

20902 - Bioprocessing technologies (industrial processes relying on biological agents to drive the process) biocatalysis, fermentation

Project

Result was created during the realization of more than one project. More information in the Projects tab.

Continuities

I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace

Publication year

2020

Confidentiality

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

Name of the periodical

Catalysts

ISSN

2073-4344

e-ISSN

—

Volume of the periodical

10

Issue of the periodical within the volume

9

Country of publishing house

CH - SWITZERLAND

Number of pages

14

Pages from-to

1077

UT code for WoS article

000581343700001

EID of the result in the Scopus database

2-s2.0-85091110004