Literature DB >> 22790719

Biotransformation of phenylacetonitrile to 2-hydroxyphenylacetic acid by marine fungi.

Julieta Rangel de Oliveira1, Carolina Megumi Mizuno, Mirna Helena Regali Seleghim, Darci Consolação Diniz Javaroti, Maria Olímpia Oliveira Rezende, Maria Diva Landgraf, Lara Durães Sette, André Luiz Meleiro Porto.   

Abstract

Marine fungi belonging to the genera Aspergillus, Penicillium, Cladosporium, and Bionectria catalyzed the biotransformation of phenylacetonitrile to 2-hydroxyphenylacetic acid. Eight marine fungi, selected and cultured with phenylacetonitrile in liquid mineral medium, catalyzed it quantitative biotransformation to 2-hydroxyphenylacetic acid. In this study, the nitrile group was firstly hydrolysed, and then, the aromatic ring was hydroxylated, producing 2-hydroxyphenylacetic acid with 51 % yield isolated. In addition, the 4-fluorophenylacetonitrile was exclusively biotransformed to 4-fluorophenylacetic acid by Aspergillus sydowii Ce19 (yield = 51 %). The enzymatic biotransformation of nitriles is not trivial, and here, we describe an efficient method for production of phenylacetic acids in mild conditions.

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Year:  2012        PMID: 22790719     DOI: 10.1007/s10126-012-9464-1

Source DB:  PubMed          Journal:  Mar Biotechnol (NY)        ISSN: 1436-2228            Impact factor:   3.619


  14 in total

Review 1.  The nitrile-degrading enzymes: current status and future prospects.

Authors:  A Banerjee; R Sharma; U C Banerjee
Journal:  Appl Microbiol Biotechnol       Date:  2002-09-06       Impact factor: 4.813

Review 2.  The nitrilase family of CN hydrolysing enzymes - a comparative study.

Authors:  C O'Reilly; P D Turner
Journal:  J Appl Microbiol       Date:  2003       Impact factor: 3.772

Review 3.  Enzymatic hydroxylation of aromatic compounds.

Authors:  René Ullrich; Martin Hofrichter
Journal:  Cell Mol Life Sci       Date:  2007-02       Impact factor: 9.261

4.  A simple and practical copper-catalyzed approach to substituted phenols from aryl halides by using water as the solvent.

Authors:  Daoshan Yang; Hua Fu
Journal:  Chemistry       Date:  2010-02-22       Impact factor: 5.236

5.  Marine fungi Aspergillus sydowii and Trichoderma sp. catalyze the hydrolysis of benzyl glycidyl ether.

Authors:  Mariana Provedel Martins; Ana Maria Mouad; Letícia Boschini; Mirna Helena Regali Seleghim; Lara Durães Sette; André Luiz Meleiro Porto
Journal:  Mar Biotechnol (NY)       Date:  2010-06-12       Impact factor: 3.619

6.  Synthesis of hydroxytyrosol, 2-hydroxyphenylacetic acid, and 3-hydroxyphenylacetic acid by differential conversion of tyrosol isomers using Serratia marcescens strain.

Authors:  Noureddine Allouche; Sami Sayadi
Journal:  J Agric Food Chem       Date:  2005-08-10       Impact factor: 5.279

7.  Biotransformation of α-bromoacetophenones by the marine fungus Aspergillus sydowii.

Authors:  Lenilson Coutinho Rocha; Hercules Vicente Ferreira; Eli Fernando Pimenta; Roberto Gomes Souza Berlinck; Maria Olímpia Oliveira Rezende; Maria Diva Landgraf; Mirna Helena Regali Seleghim; Lara Durães Sette; André Luiz Meleiro Porto
Journal:  Mar Biotechnol (NY)       Date:  2009-11-27       Impact factor: 3.619

8.  A new nitrilase from Bradyrhizobium japonicum USDA 110. Gene cloning, biochemical characterization and substrate specificity.

Authors:  Dunming Zhu; Chandrani Mukherjee; Yan Yang; Beatriz E Rios; D Travis Gallagher; N Natasha Smith; Edward R Biehl; Ling Hua
Journal:  J Biotechnol       Date:  2007-10-10       Impact factor: 3.307

9.  Isolation and characterization of a nitrile hydrolysing acidotolerant black yeast-Exophiala oligosperma R1.

Authors:  Sven Rustler; Andreas Stolz
Journal:  Appl Microbiol Biotechnol       Date:  2007-03-15       Impact factor: 4.813

10.  Characterisation of the substrate specificity of the nitrile hydrolyzing system of the acidotolerant black yeast Exophiala oligosperma R1.

Authors:  S Rustler; A Chmura; R A Sheldon; A Stolz
Journal:  Stud Mycol       Date:  2008       Impact factor: 16.097

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  4 in total

1.  Biotransformation of methylphenylacetonitriles by Brazilian marine fungal strain Aspergillus sydowii CBMAI 934: eco-friendly reactions.

Authors:  Julieta Rangel de Oliveira; Mirna Helena Regali Seleghim; André Luiz Meleiro Porto
Journal:  Mar Biotechnol (NY)       Date:  2013-09-22       Impact factor: 3.619

2.  A New Perspective on Sustainable Soil Remediation-Case Study Suggests Novel Fungal Genera Could Facilitate in situ Biodegradation of Hazardous Contaminants.

Authors:  L M Czaplicki; E Cooper; P L Ferguson; H M Stapleton; R Vilgalys; C K Gunsch
Journal:  Remediation (N Y)       Date:  2016-03-02

3.  Marine Microorganisms for Biocatalysis: Selective Hydrolysis of Nitriles with a Salt-Resistant Strain of Meyerozyma guilliermondii.

Authors:  Immacolata Serra; Claudia Capusoni; Francesco Molinari; Loana Musso; Luisa Pellegrino; Concetta Compagno
Journal:  Mar Biotechnol (NY)       Date:  2019-01-25       Impact factor: 3.619

Review 4.  Applications of Marine-Derived Microorganisms and Their Enzymes in Biocatalysis and Biotransformation, the Underexplored Potentials.

Authors:  Willian G Birolli; Rafaely N Lima; André L M Porto
Journal:  Front Microbiol       Date:  2019-08-20       Impact factor: 5.640

  4 in total

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