Deracemization of (RS)-1-[(4-Methylselanyl)Phenyl]Ethanol and
(RS)-1-[(4-Ethylselanyl)Phenyl]Ethanol by Strains of Aspergillus terreus

Leonardo Fernandes Assis¹, Edna Kagohara¹, Álvaro Takeo Omori¹, João Valdir Comasseto¹, Leandro Helgueira Andrade¹ and André Luiz Meleiro Porto^1,2*

¹Laboratório de Química Fina e Biocatálise, Instituto de Química, Universidade de São Paulo, Av. Prof. Lineu Prestes 748, CEP 05508-900, São Paulo, SP, Brazil
²Laboratório de Química Orgânica e Biocatálise, Instituto de Química de São Carlos, Universidade de São Paulo, Av. Trabalhador São-Carlense 400, CEP 13566-590, São Carlos, SP, Brazil

Article history:
Received June 29, 2006
Accepted December 14, 2006

Key words:
Aspergillus terreus, biotransformation, chiral organoseleno alcohols, fungal cells, deracemization

Summary:
The fungal strains Aspergillus terreus URM 3371 and A. terreus CCT 4083, isolated in Brazil, catalysed the deracemization of (RS)-1-[(4-methylselanyl)phenyl]ethanol (1) and (RS)-1-[(4-ethylselanyl)phenyl]ethanol (2). Different mass of whole fungal cells (1–5 g), pH values (4 and 7), biotransformation temperature (20 and 32 °C) and additives (ethanol, butanol, propanol and cyclohexanol) were employed in attempt to improve product yield and selectivity. The A. terreus strain URM 3371 transformed (RS)-1 into (+)-(R)-1 with high enantiomeric excess (e.e.≥98 %), good conversion (≥98 %) and acceptable yield (53 %).

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