Literature DB >> 16683134

Regioselective carboxylation of 1,3-dihydroxybenzene by 2,6-dihydroxybenzoate decarboxylase of Pandoraea sp. 12B-2.

Tsuyoshi Matsui1, Toyokazu Yoshida, Tomohiro Yoshimura, Toru Nagasawa.   

Abstract

We found a bacterium, Pandoraea sp. 12B-2, of which whole cells catalyzed not only the decarboxylation of 2,6-dihydroxybenzoate but also the regioselective carboxylation of 1,3-dihydroxybenzene to 2,6-dihydroxybenzoate. The whole cells of Pandoraea sp. 12B-2 also catalyzed the regioselective carboxylation of phenol and 1,2-dihydroxybenzene to 4-hydroxybenzoate and 2,3-dihydroxybenzoate, respectively. The molar conversion ratio of the carboxylation reaction depended on the concentration of KHCO(3) in the reaction mixture. Only 5 or 48 % of 1,3-dihydroxybenzene added was converted into 2,6-dihydroxybenzoate in the presence of 0.1 M or 3 M KHCO(3), respectively. The addition of acetone to the reaction mixture increased the initial rate of the carboxylation reaction, but the final molar conversion yield reached almost the same value. When the efficient production of 2,6-dihydroxybenzoate was optimized using the whole cells of Pandoraea sp. 12B-2, the productivity of 2,6-dihydroxybenzoate topped out at 1.43 M, which was the highest value so far reported. No formation of any other products was observed after the carboxylation reaction.

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Year:  2006        PMID: 16683134     DOI: 10.1007/s00253-006-0437-z

Source DB:  PubMed          Journal:  Appl Microbiol Biotechnol        ISSN: 0175-7598            Impact factor:   4.813


  11 in total

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Journal:  Appl Environ Microbiol       Date:  2015-08-28       Impact factor: 4.792

2.  Mechanism and Structure of γ-Resorcylate Decarboxylase.

Authors:  Xiang Sheng; Yury Patskovsky; Anna Vladimirova; Jeffrey B Bonanno; Steven C Almo; Fahmi Himo; Frank M Raushel
Journal:  Biochemistry       Date:  2018-01-19       Impact factor: 3.162

3.  Biochemical and genetic analysis of the gamma-resorcylate (2,6-dihydroxybenzoate) catabolic pathway in Rhizobium sp. strain MTP-10005: identification and functional analysis of its gene cluster.

Authors:  Masahiro Yoshida; Tadao Oikawa; Hitoshi Obata; Katsumasa Abe; Hisaaki Mihara; Nobuyoshi Esaki
Journal:  J Bacteriol       Date:  2006-12-08       Impact factor: 3.490

4.  Regioselective enzymatic carboxylation of phenols and hydroxystyrene derivatives.

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Journal:  Org Lett       Date:  2012-04-03       Impact factor: 6.005

5.  Regioselective Enzymatic β-Carboxylation of para-Hydroxy- styrene Derivatives Catalyzed by Phenolic Acid Decarboxylases.

Authors:  Christiane Wuensch; Tea Pavkov-Keller; Georg Steinkellner; Johannes Gross; Michael Fuchs; Altijana Hromic; Andrzej Lyskowski; Kerstin Fauland; Karl Gruber; Silvia M Glueck; Kurt Faber
Journal:  Adv Synth Catal       Date:  2015-04-02       Impact factor: 5.837

6.  Regioselective Enzymatic Carboxylation of Bioactive (Poly)phenols.

Authors:  Katharina Plasch; Verena Resch; Julien Hitce; Jarosław Popłoński; Kurt Faber; Silvia M Glueck
Journal:  Adv Synth Catal       Date:  2017-01-18       Impact factor: 5.837

7.  Pressurized CO2 as a carboxylating agent for the biocatalytic ortho-carboxylation of resorcinol.

Authors:  Katharina Plasch; Gerhard Hofer; Walter Keller; Sam Hay; Derren J Heyes; Alexander Dennig; Silvia M Glueck; Kurt Faber
Journal:  Green Chem       Date:  2018-04-03       Impact factor: 10.182

8.  Regioselective para-Carboxylation of Catechols with a Prenylated Flavin Dependent Decarboxylase.

Authors:  Stefan E Payer; Stephen A Marshall; Natalie Bärland; Xiang Sheng; Tamara Reiter; Andela Dordic; Georg Steinkellner; Christiane Wuensch; Susann Kaltwasser; Karl Fisher; Stephen E J Rigby; Peter Macheroux; Janet Vonck; Karl Gruber; Kurt Faber; Fahmi Himo; David Leys; Tea Pavkov-Keller; Silvia M Glueck
Journal:  Angew Chem Int Ed Engl       Date:  2017-10-02       Impact factor: 15.336

9.  Terminal Alkenes from Acrylic Acid Derivatives via Non-Oxidative Enzymatic Decarboxylation by Ferulic Acid Decarboxylases.

Authors:  Godwin A Aleku; Christoph Prause; Ruth T Bradshaw-Allen; Katharina Plasch; Silvia M Glueck; Samuel S Bailey; Karl A P Payne; David A Parker; Kurt Faber; David Leys
Journal:  ChemCatChem       Date:  2018-07-17       Impact factor: 5.686

10.  Metal Ion Promiscuity and Structure of 2,3-Dihydroxybenzoic Acid Decarboxylase of Aspergillus oryzae.

Authors:  Gerhard Hofer; Xiang Sheng; Simone Braeuer; Stefan E Payer; Katharina Plasch; Walter Goessler; Kurt Faber; Walter Keller; Fahmi Himo; Silvia M Glueck
Journal:  Chembiochem       Date:  2020-11-23       Impact factor: 3.164

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