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Open AccessArticle

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

1
Laboratory of Biotransformation, Institute of Microbiology of the Czech Academy of Sciences, Vídeňská 1083, CZ-142 20 Prague, Czech Republic
2
Centre for Nanobiology and Structural Biology, Institute of Microbiology of the Czech Academy of Sciences, Zámek 136, CZ-373 33 Nové Hrady, Czech Republic
3
Laboratory of Molecular Structure Characterization, Institute of Microbiology of the Czech Academy of Sciences, Vídeňská 1083, CZ-142 20 Prague, Czech Republic
*
Author to whom correspondence should be addressed.
Catalysts 2020, 10(9), 1077; https://doi.org/10.3390/catal10091077
Received: 30 June 2020 / Revised: 4 September 2020 / Accepted: 12 September 2020 / Published: 18 September 2020
(This article belongs to the Special Issue Biocatalysis in Food Technology and Processing)
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 (1b7b) were obtained in one pot by (i) oxidation of phenols 1a7a 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 1a5a. 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. View Full-Text
Keywords: biocatalyzed reaction; tyrosinase; alkylphenol; alkylcatechol; functional food; homology modeling; ligand docking biocatalyzed reaction; tyrosinase; alkylphenol; alkylcatechol; functional food; homology modeling; ligand docking
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MDPI and ACS Style

Martínková, L.; Příhodová, R.; Kulik, N.; Pelantová, H.; Křístková, B.; Petrásková, L.; Biedermann, D. Biocatalyzed Reactions towards Functional Food Components 4-Alkylcatechols and Their Analogues. Catalysts 2020, 10, 1077.

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