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

Catechols are antioxidants and radical scavengers with a broad medical potential. 4-Methylcatechol (<b<1b</b<) and 4-ethylcatechol (<b<2b</b<) (occurring in some traditional fermented and smoked foods) activate the cell defense against oxidative stress. We examined the biocat...
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Autor*in:	Ludmila Martínková [verfasserIn] Romana Příhodová [verfasserIn] Natalia Kulik [verfasserIn] Helena Pelantová [verfasserIn] Barbora Křístková [verfasserIn] Lucie Petrásková [verfasserIn] David Biedermann [verfasserIn]

Format:	E-Artikel
Sprache:	Englisch

Erschienen:	2020

Schlagwörter:	biocatalyzed reaction tyrosinase alkylphenol alkylcatechol functional food homology modeling

Übergeordnetes Werk:	In: Catalysts - MDPI AG, 2012, 10(2020), 9, p 1077
Übergeordnetes Werk:	volume:10 ; year:2020 ; number:9, p 1077

Links:	Link aufrufen Link aufrufen Link aufrufen Journal toc

DOI / URN:	10.3390/catal10091077

Katalog-ID:	DOAJ073989711

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allfields	10.3390/catal10091077 doi (DE-627)DOAJ073989711 (DE-599)DOAJea9809766cdd4a3085a6107376f38bf0 DE-627 ger DE-627 rakwb eng TP1-1185 QD1-999 Ludmila Martínková verfasserin aut Biocatalyzed Reactions towards Functional Food Components 4-Alkylcatechols and Their Analogues 2020 Text txt rdacontent Computermedien c rdamedia Online-Ressource cr rdacarrier Catechols are antioxidants and radical scavengers with a broad medical potential. 4-Methylcatechol (<b<1b</b<) and 4-ethylcatechol (<b<2b</b<) (occurring in some traditional fermented and smoked foods) activate the cell defense against oxidative stress. We examined the biocatalyzed reactions towards 4-<i<n</i<-alkylcatechols with different side chains length, which is a factor important for the biological activities of catechols. 4-<i<n</i<-Alkylcatechols with methyl through heptyl side chains (<b<1b</b<–<b<7b</b<) were obtained in one pot by (i) oxidation of phenols <b<1a</b<–<b<7a</b< with tyrosinase from <i<Agaricus bisporus</i< followed by (ii) reduction of <i<ortho</i<-quinones (intermediates) with L-ascorbic acid sodium salt. The conversions decreased with increasing side chain length. The preparative reactions were carried out with substrates <b<1a</b<–<b<5a</b<. The isolated yields of the purified products decreased from 59% in <b<2b</b< to 10% in <b<5b</b< 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. biocatalyzed reaction tyrosinase alkylphenol alkylcatechol functional food homology modeling Chemical technology Chemistry Romana Příhodová verfasserin aut Natalia Kulik verfasserin aut Helena Pelantová verfasserin aut Barbora Křístková verfasserin aut Lucie Petrásková verfasserin aut David Biedermann verfasserin aut In Catalysts MDPI AG, 2012 10(2020), 9, p 1077 (DE-627)71862646X (DE-600)2662126-5 20734344 nnns volume:10 year:2020 number:9, p 1077 https://doi.org/10.3390/catal10091077 kostenfrei https://doaj.org/article/ea9809766cdd4a3085a6107376f38bf0 kostenfrei https://www.mdpi.com/2073-4344/10/9/1077 kostenfrei https://doaj.org/toc/2073-4344 Journal toc kostenfrei GBV_USEFLAG_A SYSFLAG_A GBV_DOAJ GBV_ILN_20 GBV_ILN_22 GBV_ILN_23 GBV_ILN_24 GBV_ILN_39 GBV_ILN_40 GBV_ILN_60 GBV_ILN_62 GBV_ILN_63 GBV_ILN_65 GBV_ILN_69 GBV_ILN_70 GBV_ILN_73 GBV_ILN_95 GBV_ILN_105 GBV_ILN_110 GBV_ILN_151 GBV_ILN_161 GBV_ILN_170 GBV_ILN_206 GBV_ILN_213 GBV_ILN_230 GBV_ILN_285 GBV_ILN_293 GBV_ILN_602 GBV_ILN_2005 GBV_ILN_2009 GBV_ILN_2011 GBV_ILN_2014 GBV_ILN_2055 GBV_ILN_2111 GBV_ILN_4012 GBV_ILN_4037 GBV_ILN_4112 GBV_ILN_4125 GBV_ILN_4126 GBV_ILN_4249 GBV_ILN_4305 GBV_ILN_4306 GBV_ILN_4307 GBV_ILN_4313 GBV_ILN_4322 GBV_ILN_4323 GBV_ILN_4324 GBV_ILN_4325 GBV_ILN_4338 GBV_ILN_4367 GBV_ILN_4700 AR 10 2020 9, p 1077
spelling	10.3390/catal10091077 doi (DE-627)DOAJ073989711 (DE-599)DOAJea9809766cdd4a3085a6107376f38bf0 DE-627 ger DE-627 rakwb eng TP1-1185 QD1-999 Ludmila Martínková verfasserin aut Biocatalyzed Reactions towards Functional Food Components 4-Alkylcatechols and Their Analogues 2020 Text txt rdacontent Computermedien c rdamedia Online-Ressource cr rdacarrier Catechols are antioxidants and radical scavengers with a broad medical potential. 4-Methylcatechol (<b<1b</b<) and 4-ethylcatechol (<b<2b</b<) (occurring in some traditional fermented and smoked foods) activate the cell defense against oxidative stress. We examined the biocatalyzed reactions towards 4-<i<n</i<-alkylcatechols with different side chains length, which is a factor important for the biological activities of catechols. 4-<i<n</i<-Alkylcatechols with methyl through heptyl side chains (<b<1b</b<–<b<7b</b<) were obtained in one pot by (i) oxidation of phenols <b<1a</b<–<b<7a</b< with tyrosinase from <i<Agaricus bisporus</i< followed by (ii) reduction of <i<ortho</i<-quinones (intermediates) with L-ascorbic acid sodium salt. The conversions decreased with increasing side chain length. The preparative reactions were carried out with substrates <b<1a</b<–<b<5a</b<. The isolated yields of the purified products decreased from 59% in <b<2b</b< to 10% in <b<5b</b< 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. biocatalyzed reaction tyrosinase alkylphenol alkylcatechol functional food homology modeling Chemical technology Chemistry Romana Příhodová verfasserin aut Natalia Kulik verfasserin aut Helena Pelantová verfasserin aut Barbora Křístková verfasserin aut Lucie Petrásková verfasserin aut David Biedermann verfasserin aut In Catalysts MDPI AG, 2012 10(2020), 9, p 1077 (DE-627)71862646X (DE-600)2662126-5 20734344 nnns volume:10 year:2020 number:9, p 1077 https://doi.org/10.3390/catal10091077 kostenfrei https://doaj.org/article/ea9809766cdd4a3085a6107376f38bf0 kostenfrei https://www.mdpi.com/2073-4344/10/9/1077 kostenfrei https://doaj.org/toc/2073-4344 Journal toc kostenfrei GBV_USEFLAG_A SYSFLAG_A GBV_DOAJ GBV_ILN_20 GBV_ILN_22 GBV_ILN_23 GBV_ILN_24 GBV_ILN_39 GBV_ILN_40 GBV_ILN_60 GBV_ILN_62 GBV_ILN_63 GBV_ILN_65 GBV_ILN_69 GBV_ILN_70 GBV_ILN_73 GBV_ILN_95 GBV_ILN_105 GBV_ILN_110 GBV_ILN_151 GBV_ILN_161 GBV_ILN_170 GBV_ILN_206 GBV_ILN_213 GBV_ILN_230 GBV_ILN_285 GBV_ILN_293 GBV_ILN_602 GBV_ILN_2005 GBV_ILN_2009 GBV_ILN_2011 GBV_ILN_2014 GBV_ILN_2055 GBV_ILN_2111 GBV_ILN_4012 GBV_ILN_4037 GBV_ILN_4112 GBV_ILN_4125 GBV_ILN_4126 GBV_ILN_4249 GBV_ILN_4305 GBV_ILN_4306 GBV_ILN_4307 GBV_ILN_4313 GBV_ILN_4322 GBV_ILN_4323 GBV_ILN_4324 GBV_ILN_4325 GBV_ILN_4338 GBV_ILN_4367 GBV_ILN_4700 AR 10 2020 9, p 1077
allfields_unstemmed	10.3390/catal10091077 doi (DE-627)DOAJ073989711 (DE-599)DOAJea9809766cdd4a3085a6107376f38bf0 DE-627 ger DE-627 rakwb eng TP1-1185 QD1-999 Ludmila Martínková verfasserin aut Biocatalyzed Reactions towards Functional Food Components 4-Alkylcatechols and Their Analogues 2020 Text txt rdacontent Computermedien c rdamedia Online-Ressource cr rdacarrier Catechols are antioxidants and radical scavengers with a broad medical potential. 4-Methylcatechol (<b<1b</b<) and 4-ethylcatechol (<b<2b</b<) (occurring in some traditional fermented and smoked foods) activate the cell defense against oxidative stress. We examined the biocatalyzed reactions towards 4-<i<n</i<-alkylcatechols with different side chains length, which is a factor important for the biological activities of catechols. 4-<i<n</i<-Alkylcatechols with methyl through heptyl side chains (<b<1b</b<–<b<7b</b<) were obtained in one pot by (i) oxidation of phenols <b<1a</b<–<b<7a</b< with tyrosinase from <i<Agaricus bisporus</i< followed by (ii) reduction of <i<ortho</i<-quinones (intermediates) with L-ascorbic acid sodium salt. The conversions decreased with increasing side chain length. The preparative reactions were carried out with substrates <b<1a</b<–<b<5a</b<. The isolated yields of the purified products decreased from 59% in <b<2b</b< to 10% in <b<5b</b< 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. biocatalyzed reaction tyrosinase alkylphenol alkylcatechol functional food homology modeling Chemical technology Chemistry Romana Příhodová verfasserin aut Natalia Kulik verfasserin aut Helena Pelantová verfasserin aut Barbora Křístková verfasserin aut Lucie Petrásková verfasserin aut David Biedermann verfasserin aut In Catalysts MDPI AG, 2012 10(2020), 9, p 1077 (DE-627)71862646X (DE-600)2662126-5 20734344 nnns volume:10 year:2020 number:9, p 1077 https://doi.org/10.3390/catal10091077 kostenfrei https://doaj.org/article/ea9809766cdd4a3085a6107376f38bf0 kostenfrei https://www.mdpi.com/2073-4344/10/9/1077 kostenfrei https://doaj.org/toc/2073-4344 Journal toc kostenfrei GBV_USEFLAG_A SYSFLAG_A GBV_DOAJ GBV_ILN_20 GBV_ILN_22 GBV_ILN_23 GBV_ILN_24 GBV_ILN_39 GBV_ILN_40 GBV_ILN_60 GBV_ILN_62 GBV_ILN_63 GBV_ILN_65 GBV_ILN_69 GBV_ILN_70 GBV_ILN_73 GBV_ILN_95 GBV_ILN_105 GBV_ILN_110 GBV_ILN_151 GBV_ILN_161 GBV_ILN_170 GBV_ILN_206 GBV_ILN_213 GBV_ILN_230 GBV_ILN_285 GBV_ILN_293 GBV_ILN_602 GBV_ILN_2005 GBV_ILN_2009 GBV_ILN_2011 GBV_ILN_2014 GBV_ILN_2055 GBV_ILN_2111 GBV_ILN_4012 GBV_ILN_4037 GBV_ILN_4112 GBV_ILN_4125 GBV_ILN_4126 GBV_ILN_4249 GBV_ILN_4305 GBV_ILN_4306 GBV_ILN_4307 GBV_ILN_4313 GBV_ILN_4322 GBV_ILN_4323 GBV_ILN_4324 GBV_ILN_4325 GBV_ILN_4338 GBV_ILN_4367 GBV_ILN_4700 AR 10 2020 9, p 1077
allfieldsGer	10.3390/catal10091077 doi (DE-627)DOAJ073989711 (DE-599)DOAJea9809766cdd4a3085a6107376f38bf0 DE-627 ger DE-627 rakwb eng TP1-1185 QD1-999 Ludmila Martínková verfasserin aut Biocatalyzed Reactions towards Functional Food Components 4-Alkylcatechols and Their Analogues 2020 Text txt rdacontent Computermedien c rdamedia Online-Ressource cr rdacarrier Catechols are antioxidants and radical scavengers with a broad medical potential. 4-Methylcatechol (<b<1b</b<) and 4-ethylcatechol (<b<2b</b<) (occurring in some traditional fermented and smoked foods) activate the cell defense against oxidative stress. We examined the biocatalyzed reactions towards 4-<i<n</i<-alkylcatechols with different side chains length, which is a factor important for the biological activities of catechols. 4-<i<n</i<-Alkylcatechols with methyl through heptyl side chains (<b<1b</b<–<b<7b</b<) were obtained in one pot by (i) oxidation of phenols <b<1a</b<–<b<7a</b< with tyrosinase from <i<Agaricus bisporus</i< followed by (ii) reduction of <i<ortho</i<-quinones (intermediates) with L-ascorbic acid sodium salt. The conversions decreased with increasing side chain length. The preparative reactions were carried out with substrates <b<1a</b<–<b<5a</b<. The isolated yields of the purified products decreased from 59% in <b<2b</b< to 10% in <b<5b</b< 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. biocatalyzed reaction tyrosinase alkylphenol alkylcatechol functional food homology modeling Chemical technology Chemistry Romana Příhodová verfasserin aut Natalia Kulik verfasserin aut Helena Pelantová verfasserin aut Barbora Křístková verfasserin aut Lucie Petrásková verfasserin aut David Biedermann verfasserin aut In Catalysts MDPI AG, 2012 10(2020), 9, p 1077 (DE-627)71862646X (DE-600)2662126-5 20734344 nnns volume:10 year:2020 number:9, p 1077 https://doi.org/10.3390/catal10091077 kostenfrei https://doaj.org/article/ea9809766cdd4a3085a6107376f38bf0 kostenfrei https://www.mdpi.com/2073-4344/10/9/1077 kostenfrei https://doaj.org/toc/2073-4344 Journal toc kostenfrei GBV_USEFLAG_A SYSFLAG_A GBV_DOAJ GBV_ILN_20 GBV_ILN_22 GBV_ILN_23 GBV_ILN_24 GBV_ILN_39 GBV_ILN_40 GBV_ILN_60 GBV_ILN_62 GBV_ILN_63 GBV_ILN_65 GBV_ILN_69 GBV_ILN_70 GBV_ILN_73 GBV_ILN_95 GBV_ILN_105 GBV_ILN_110 GBV_ILN_151 GBV_ILN_161 GBV_ILN_170 GBV_ILN_206 GBV_ILN_213 GBV_ILN_230 GBV_ILN_285 GBV_ILN_293 GBV_ILN_602 GBV_ILN_2005 GBV_ILN_2009 GBV_ILN_2011 GBV_ILN_2014 GBV_ILN_2055 GBV_ILN_2111 GBV_ILN_4012 GBV_ILN_4037 GBV_ILN_4112 GBV_ILN_4125 GBV_ILN_4126 GBV_ILN_4249 GBV_ILN_4305 GBV_ILN_4306 GBV_ILN_4307 GBV_ILN_4313 GBV_ILN_4322 GBV_ILN_4323 GBV_ILN_4324 GBV_ILN_4325 GBV_ILN_4338 GBV_ILN_4367 GBV_ILN_4700 AR 10 2020 9, p 1077
allfieldsSound	10.3390/catal10091077 doi (DE-627)DOAJ073989711 (DE-599)DOAJea9809766cdd4a3085a6107376f38bf0 DE-627 ger DE-627 rakwb eng TP1-1185 QD1-999 Ludmila Martínková verfasserin aut Biocatalyzed Reactions towards Functional Food Components 4-Alkylcatechols and Their Analogues 2020 Text txt rdacontent Computermedien c rdamedia Online-Ressource cr rdacarrier Catechols are antioxidants and radical scavengers with a broad medical potential. 4-Methylcatechol (<b<1b</b<) and 4-ethylcatechol (<b<2b</b<) (occurring in some traditional fermented and smoked foods) activate the cell defense against oxidative stress. We examined the biocatalyzed reactions towards 4-<i<n</i<-alkylcatechols with different side chains length, which is a factor important for the biological activities of catechols. 4-<i<n</i<-Alkylcatechols with methyl through heptyl side chains (<b<1b</b<–<b<7b</b<) were obtained in one pot by (i) oxidation of phenols <b<1a</b<–<b<7a</b< with tyrosinase from <i<Agaricus bisporus</i< followed by (ii) reduction of <i<ortho</i<-quinones (intermediates) with L-ascorbic acid sodium salt. The conversions decreased with increasing side chain length. The preparative reactions were carried out with substrates <b<1a</b<–<b<5a</b<. The isolated yields of the purified products decreased from 59% in <b<2b</b< to 10% in <b<5b</b< 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. biocatalyzed reaction tyrosinase alkylphenol alkylcatechol functional food homology modeling Chemical technology Chemistry Romana Příhodová verfasserin aut Natalia Kulik verfasserin aut Helena Pelantová verfasserin aut Barbora Křístková verfasserin aut Lucie Petrásková verfasserin aut David Biedermann verfasserin aut In Catalysts MDPI AG, 2012 10(2020), 9, p 1077 (DE-627)71862646X (DE-600)2662126-5 20734344 nnns volume:10 year:2020 number:9, p 1077 https://doi.org/10.3390/catal10091077 kostenfrei https://doaj.org/article/ea9809766cdd4a3085a6107376f38bf0 kostenfrei https://www.mdpi.com/2073-4344/10/9/1077 kostenfrei https://doaj.org/toc/2073-4344 Journal toc kostenfrei GBV_USEFLAG_A SYSFLAG_A GBV_DOAJ GBV_ILN_20 GBV_ILN_22 GBV_ILN_23 GBV_ILN_24 GBV_ILN_39 GBV_ILN_40 GBV_ILN_60 GBV_ILN_62 GBV_ILN_63 GBV_ILN_65 GBV_ILN_69 GBV_ILN_70 GBV_ILN_73 GBV_ILN_95 GBV_ILN_105 GBV_ILN_110 GBV_ILN_151 GBV_ILN_161 GBV_ILN_170 GBV_ILN_206 GBV_ILN_213 GBV_ILN_230 GBV_ILN_285 GBV_ILN_293 GBV_ILN_602 GBV_ILN_2005 GBV_ILN_2009 GBV_ILN_2011 GBV_ILN_2014 GBV_ILN_2055 GBV_ILN_2111 GBV_ILN_4012 GBV_ILN_4037 GBV_ILN_4112 GBV_ILN_4125 GBV_ILN_4126 GBV_ILN_4249 GBV_ILN_4305 GBV_ILN_4306 GBV_ILN_4307 GBV_ILN_4313 GBV_ILN_4322 GBV_ILN_4323 GBV_ILN_4324 GBV_ILN_4325 GBV_ILN_4338 GBV_ILN_4367 GBV_ILN_4700 AR 10 2020 9, p 1077
language	English
source	In Catalysts 10(2020), 9, p 1077 volume:10 year:2020 number:9, p 1077
sourceStr	In Catalysts 10(2020), 9, p 1077 volume:10 year:2020 number:9, p 1077
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topic_facet	biocatalyzed reaction tyrosinase alkylphenol alkylcatechol functional food homology modeling Chemical technology Chemistry
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container_title	Catalysts
authorswithroles_txt_mv	Ludmila Martínková @@aut@@ Romana Příhodová @@aut@@ Natalia Kulik @@aut@@ Helena Pelantová @@aut@@ Barbora Křístková @@aut@@ Lucie Petrásková @@aut@@ David Biedermann @@aut@@
publishDateDaySort_date	2020-01-01T00:00:00Z
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author	Ludmila Martínková
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issn	20734344
topic_title	TP1-1185 QD1-999 Biocatalyzed Reactions towards Functional Food Components 4-Alkylcatechols and Their Analogues biocatalyzed reaction tyrosinase alkylphenol alkylcatechol functional food homology modeling
topic	misc TP1-1185 misc QD1-999 misc biocatalyzed reaction misc tyrosinase misc alkylphenol misc alkylcatechol misc functional food misc homology modeling misc Chemical technology misc Chemistry
topic_unstemmed	misc TP1-1185 misc QD1-999 misc biocatalyzed reaction misc tyrosinase misc alkylphenol misc alkylcatechol misc functional food misc homology modeling misc Chemical technology misc Chemistry
topic_browse	misc TP1-1185 misc QD1-999 misc biocatalyzed reaction misc tyrosinase misc alkylphenol misc alkylcatechol misc functional food misc homology modeling misc Chemical technology misc Chemistry
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title	Biocatalyzed Reactions towards Functional Food Components 4-Alkylcatechols and Their Analogues
ctrlnum	(DE-627)DOAJ073989711 (DE-599)DOAJea9809766cdd4a3085a6107376f38bf0
title_full	Biocatalyzed Reactions towards Functional Food Components 4-Alkylcatechols and Their Analogues
author_sort	Ludmila Martínková
journal	Catalysts
journalStr	Catalysts
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author_browse	Ludmila Martínková Romana Příhodová Natalia Kulik Helena Pelantová Barbora Křístková Lucie Petrásková David Biedermann
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class	TP1-1185 QD1-999
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author-letter	Ludmila Martínková
doi_str_mv	10.3390/catal10091077
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title_sort	biocatalyzed reactions towards functional food components 4-alkylcatechols and their analogues
callnumber	TP1-1185
title_auth	Biocatalyzed Reactions towards Functional Food Components 4-Alkylcatechols and Their Analogues
abstract	Catechols are antioxidants and radical scavengers with a broad medical potential. 4-Methylcatechol (<b<1b</b<) and 4-ethylcatechol (<b<2b</b<) (occurring in some traditional fermented and smoked foods) activate the cell defense against oxidative stress. We examined the biocatalyzed reactions towards 4-<i<n</i<-alkylcatechols with different side chains length, which is a factor important for the biological activities of catechols. 4-<i<n</i<-Alkylcatechols with methyl through heptyl side chains (<b<1b</b<–<b<7b</b<) were obtained in one pot by (i) oxidation of phenols <b<1a</b<–<b<7a</b< with tyrosinase from <i<Agaricus bisporus</i< followed by (ii) reduction of <i<ortho</i<-quinones (intermediates) with L-ascorbic acid sodium salt. The conversions decreased with increasing side chain length. The preparative reactions were carried out with substrates <b<1a</b<–<b<5a</b<. The isolated yields of the purified products decreased from 59% in <b<2b</b< to 10% in <b<5b</b< 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.
abstractGer	Catechols are antioxidants and radical scavengers with a broad medical potential. 4-Methylcatechol (<b<1b</b<) and 4-ethylcatechol (<b<2b</b<) (occurring in some traditional fermented and smoked foods) activate the cell defense against oxidative stress. We examined the biocatalyzed reactions towards 4-<i<n</i<-alkylcatechols with different side chains length, which is a factor important for the biological activities of catechols. 4-<i<n</i<-Alkylcatechols with methyl through heptyl side chains (<b<1b</b<–<b<7b</b<) were obtained in one pot by (i) oxidation of phenols <b<1a</b<–<b<7a</b< with tyrosinase from <i<Agaricus bisporus</i< followed by (ii) reduction of <i<ortho</i<-quinones (intermediates) with L-ascorbic acid sodium salt. The conversions decreased with increasing side chain length. The preparative reactions were carried out with substrates <b<1a</b<–<b<5a</b<. The isolated yields of the purified products decreased from 59% in <b<2b</b< to 10% in <b<5b</b< 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.
abstract_unstemmed	Catechols are antioxidants and radical scavengers with a broad medical potential. 4-Methylcatechol (<b<1b</b<) and 4-ethylcatechol (<b<2b</b<) (occurring in some traditional fermented and smoked foods) activate the cell defense against oxidative stress. We examined the biocatalyzed reactions towards 4-<i<n</i<-alkylcatechols with different side chains length, which is a factor important for the biological activities of catechols. 4-<i<n</i<-Alkylcatechols with methyl through heptyl side chains (<b<1b</b<–<b<7b</b<) were obtained in one pot by (i) oxidation of phenols <b<1a</b<–<b<7a</b< with tyrosinase from <i<Agaricus bisporus</i< followed by (ii) reduction of <i<ortho</i<-quinones (intermediates) with L-ascorbic acid sodium salt. The conversions decreased with increasing side chain length. The preparative reactions were carried out with substrates <b<1a</b<–<b<5a</b<. The isolated yields of the purified products decreased from 59% in <b<2b</b< to 10% in <b<5b</b< 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.
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container_issue	9, p 1077
title_short	Biocatalyzed Reactions towards Functional Food Components 4-Alkylcatechols and Their Analogues
url	https://doi.org/10.3390/catal10091077 https://doaj.org/article/ea9809766cdd4a3085a6107376f38bf0 https://www.mdpi.com/2073-4344/10/9/1077 https://doaj.org/toc/2073-4344
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author2	Romana Příhodová Natalia Kulik Helena Pelantová Barbora Křístková Lucie Petrásková David Biedermann
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up_date	2024-07-03T20:43:30.641Z
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