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Demethylation of N,N-Dimethylbenzenamine and N,N,3-Trimethylbenzenamine by Whole Cells of Aspergillus terreus

Leandro Piovan1, Edna Kagohara1, Juliana Alves Vale1, João Valdir Comasseto1, Iracema Helena Schoenlein-Crusius2, Leandro Helgueira Andrade1and André Luiz Meleiro Porto1,3*


1Institute of Chemistry of São Paulo, University of São Paulo, Av. Prof. Lineu Prestes, 748,
CEP 05508-900, São Paulo-SP, Brazil
2Institute of Botany of São Paulo, Section of Mycology and Lichenology, Av. Miguel Stéfano, 3687, CEP 01061-970, São Paulo-SP, Brazil
3Institute of Chemistry of São Carlos, University of São Paulo, Av. Trabalhador São-Carlense, 400, CEP 13566-590, São Carlos-SP, Brazil

Article history:

Received June 28, 2010
Accepted October 1, 2010

Key words:

Aspergillus terreus, N-demethylation, tertiary aromatic amines, biotransformation

Summary:

N,N-dimethylbenzenamine and N,N,3-trimethylbenzenamine were N-demethylated through enzymatic reactions mediated by whole cells of Aspergillus terreus strains SSP 1498, URM 3371 and URM 3571. The respective products, N-methylbenzenamine and N,3-dimethylbenzenamine, were obtained in high conversions under both neutral and basic conditions. The oxidative N-demethylation of tertiary aromatic amines by A. terreus was not enhanced by the presence of the oxidant tert-butylperoxide, although further demethylation of N,N-dimethylbenzenamine to aniline was observed. The strains of the investigated A. terreus were unable to perform the dealkylation of N,N-diethylbenzenamine.


*Corresponding author:           almporto@iqsc.usp.br
                                               ++55 16 3373 8103
                                               ++55 16 3373 9952

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