Cover Image

Membrane-associated glucose-methanol-choline oxidoreductase family enzymes PhcC and PhcD are essential for enantioselective catabolism of dehydrodiconiferyl alcohol

Sphingobium sp. strain SYK-6 is able to degrade various lignin-derived biaryls, including a phenylcoumaran-type compound, dehydrodiconiferyl alcohol (DCA). In SYK-6 cells, the alcohol group of the B-ring side chain of DCA is initially oxidized to the carboxyl group to generate 3-(2-(4-hydroxy-3-meth...

Full description

Saved in:
Bibliographic Details
Main Authors: Takahashi, Kenji, Hirose, Yusaku, Kamimura, Naofumi, Hishiyama, Shojiro, Hara, Hirofumi, Araki, Takuma, Kasai, Daisuke, Kajita, Shinya, Katayama, Yoshihiro, Fukuda, Masao, Masai, Eiji
Format: Article
Language:English
Published: American Society for Microbiology 2015
Subjects:
TA Engineering (General). Civil engineering (General)
TP Chemical technology
Online Access:http://eprints.utm.my/id/eprint/58527/1/HirofumiHara2015_MembraneAssociatedGlucoseMethanolCholine.pdf
http://eprints.utm.my/id/eprint/58527/
http://dx.doi.org/10.1128/AEM.02391-15
Tags: Add Tag
No Tags, Be the first to tag this record!
id my.utm.58527
record_format eprints
spelling my.utm.585272021-09-05T02:21:01Z http://eprints.utm.my/id/eprint/58527/ Membrane-associated glucose-methanol-choline oxidoreductase family enzymes PhcC and PhcD are essential for enantioselective catabolism of dehydrodiconiferyl alcohol Takahashi, Kenji Hirose, Yusaku Kamimura, Naofumi Hishiyama, Shojiro Hara, Hirofumi Araki, Takuma Kasai, Daisuke Kajita, Shinya Katayama, Yoshihiro Fukuda, Masao Masai, Eiji TA Engineering (General). Civil engineering (General) TP Chemical technology Sphingobium sp. strain SYK-6 is able to degrade various lignin-derived biaryls, including a phenylcoumaran-type compound, dehydrodiconiferyl alcohol (DCA). In SYK-6 cells, the alcohol group of the B-ring side chain of DCA is initially oxidized to the carboxyl group to generate 3-(2-(4-hydroxy-3-methoxyphenyl)-3-(hydroxymethyl)-7-methoxy-2,3-dihydrobenzofuran-5-yl) acrylic acid (DCA-C). Next, the alcohol group of the A-ring side chain of DCA-C is oxidized to the carboxyl group, and then the resulting metabolite is catabolized through vanillin and 5-formylferulate. In this study, the genes involved in the conversion of DCA-C were identified and characterized. The DCA-C oxidation activities in SYK-6 were enhanced in the presence of flavin adenine dinucleotide and an artificial electron acceptor and were induced ca. 1.6-fold when the cells were grown with DCA. Based on these observations, SLG_09480 (phcC) and SLG_09500 (phcD), encoding glucose-methanol-choline oxidoreductase family proteins, were presumed to encode DCA-C oxidases. Analyses of phcC and phcD mutants indicated that PhcC and PhcD are essential for the conversion of (+)-DCA-C and (-)-DCA-C, respectively. When phcC and phcD were expressed in SYK-6 and Escherichia coli, the gene products were mainly observed in their membrane fractions. The membrane fractions of E. coli that expressed phcC and phcD catalyzed the specific conversion of DCA-C into the corresponding carboxyl derivatives. In the oxidation of DCA-C, PhcC and PhcD effectively utilized ubiquinone derivatives as electron acceptors. Furthermore, the transcription of a putative cytochrome c gene was significantly induced in SYK-6 grown with DCA. The DCA-C oxidation catalyzed by membrane- associated PhcC and PhcD appears to be coupled to the respiratory chain. American Society for Microbiology 2015 Article PeerReviewed application/pdf en http://eprints.utm.my/id/eprint/58527/1/HirofumiHara2015_MembraneAssociatedGlucoseMethanolCholine.pdf Takahashi, Kenji and Hirose, Yusaku and Kamimura, Naofumi and Hishiyama, Shojiro and Hara, Hirofumi and Araki, Takuma and Kasai, Daisuke and Kajita, Shinya and Katayama, Yoshihiro and Fukuda, Masao and Masai, Eiji (2015) Membrane-associated glucose-methanol-choline oxidoreductase family enzymes PhcC and PhcD are essential for enantioselective catabolism of dehydrodiconiferyl alcohol. Applied And Environmental Microbiology, 81 (23). pp. 8022-8036. ISSN 0099-2240 http://dx.doi.org/10.1128/AEM.02391-15 DOI:10.1128/AEM.02391-15
institution Universiti Teknologi Malaysia
building UTM Library
collection Institutional Repository
continent Asia
country Malaysia
content_provider Universiti Teknologi Malaysia
content_source UTM Institutional Repository
url_provider http://eprints.utm.my/
language English
topic TA Engineering (General). Civil engineering (General)
TP Chemical technology
spellingShingle TA Engineering (General). Civil engineering (General)
TP Chemical technology
Takahashi, Kenji
Hirose, Yusaku
Kamimura, Naofumi
Hishiyama, Shojiro
Hara, Hirofumi
Araki, Takuma
Kasai, Daisuke
Kajita, Shinya
Katayama, Yoshihiro
Fukuda, Masao
Masai, Eiji
Membrane-associated glucose-methanol-choline oxidoreductase family enzymes PhcC and PhcD are essential for enantioselective catabolism of dehydrodiconiferyl alcohol
description Sphingobium sp. strain SYK-6 is able to degrade various lignin-derived biaryls, including a phenylcoumaran-type compound, dehydrodiconiferyl alcohol (DCA). In SYK-6 cells, the alcohol group of the B-ring side chain of DCA is initially oxidized to the carboxyl group to generate 3-(2-(4-hydroxy-3-methoxyphenyl)-3-(hydroxymethyl)-7-methoxy-2,3-dihydrobenzofuran-5-yl) acrylic acid (DCA-C). Next, the alcohol group of the A-ring side chain of DCA-C is oxidized to the carboxyl group, and then the resulting metabolite is catabolized through vanillin and 5-formylferulate. In this study, the genes involved in the conversion of DCA-C were identified and characterized. The DCA-C oxidation activities in SYK-6 were enhanced in the presence of flavin adenine dinucleotide and an artificial electron acceptor and were induced ca. 1.6-fold when the cells were grown with DCA. Based on these observations, SLG_09480 (phcC) and SLG_09500 (phcD), encoding glucose-methanol-choline oxidoreductase family proteins, were presumed to encode DCA-C oxidases. Analyses of phcC and phcD mutants indicated that PhcC and PhcD are essential for the conversion of (+)-DCA-C and (-)-DCA-C, respectively. When phcC and phcD were expressed in SYK-6 and Escherichia coli, the gene products were mainly observed in their membrane fractions. The membrane fractions of E. coli that expressed phcC and phcD catalyzed the specific conversion of DCA-C into the corresponding carboxyl derivatives. In the oxidation of DCA-C, PhcC and PhcD effectively utilized ubiquinone derivatives as electron acceptors. Furthermore, the transcription of a putative cytochrome c gene was significantly induced in SYK-6 grown with DCA. The DCA-C oxidation catalyzed by membrane- associated PhcC and PhcD appears to be coupled to the respiratory chain.
format Article
author Takahashi, Kenji
Hirose, Yusaku
Kamimura, Naofumi
Hishiyama, Shojiro
Hara, Hirofumi
Araki, Takuma
Kasai, Daisuke
Kajita, Shinya
Katayama, Yoshihiro
Fukuda, Masao
Masai, Eiji
author_facet Takahashi, Kenji
Hirose, Yusaku
Kamimura, Naofumi
Hishiyama, Shojiro
Hara, Hirofumi
Araki, Takuma
Kasai, Daisuke
Kajita, Shinya
Katayama, Yoshihiro
Fukuda, Masao
Masai, Eiji
author_sort Takahashi, Kenji
title Membrane-associated glucose-methanol-choline oxidoreductase family enzymes PhcC and PhcD are essential for enantioselective catabolism of dehydrodiconiferyl alcohol
title_short Membrane-associated glucose-methanol-choline oxidoreductase family enzymes PhcC and PhcD are essential for enantioselective catabolism of dehydrodiconiferyl alcohol
title_full Membrane-associated glucose-methanol-choline oxidoreductase family enzymes PhcC and PhcD are essential for enantioselective catabolism of dehydrodiconiferyl alcohol
title_fullStr Membrane-associated glucose-methanol-choline oxidoreductase family enzymes PhcC and PhcD are essential for enantioselective catabolism of dehydrodiconiferyl alcohol
title_full_unstemmed Membrane-associated glucose-methanol-choline oxidoreductase family enzymes PhcC and PhcD are essential for enantioselective catabolism of dehydrodiconiferyl alcohol
title_sort membrane-associated glucose-methanol-choline oxidoreductase family enzymes phcc and phcd are essential for enantioselective catabolism of dehydrodiconiferyl alcohol
publisher American Society for Microbiology
publishDate 2015
url http://eprints.utm.my/id/eprint/58527/1/HirofumiHara2015_MembraneAssociatedGlucoseMethanolCholine.pdf
http://eprints.utm.my/id/eprint/58527/
http://dx.doi.org/10.1128/AEM.02391-15
_version_ 1712285037306576896
score 13.211869

Similar Items