Biotransformation of phenylacetonitrile to 2-hydroxyphenylacetic acid by marine fungi.
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.
Instituto de Química de São Carlos, Universidade de São Paulo, Av. Trabalhador São-carlense 400, CEP 13560-970, CP 780, São Carlos, SP, Brazil.
Julieta Rangel
JR
de Oliveira
Carolina Megumi
CM
Mizuno
Mirna Helena Regali
MH
Seleghim
Darci Consolação Diniz
DC
Javaroti
Maria Olímpia Oliveira
MO
Rezende
Maria Diva
MD
Landgraf
Lara Durães
LD
Sette
André Luiz Meleiro
AL
Porto
D000097:Acetonitriles / Q000378:metabolism*; D001711:Biotransformation / Q000502:physiology*; D002384:Catalysis; D005658:Fungi / Q000254:growth & development / Q000378:metabolism / Q000502:physiology*; D006868:Hydrolysis; D006900:Hydroxylation; D008386:Marine Biology; D010648:Phenylacetates / Q000302:isolation & purification / Q000378:metabolism*
D000097:Acetonitriles; D010648:Phenylacetates; C006725:benzyl cyanide; C005756:2-hydroxyphenylacetic acid