Bioreduction of alpha-chloroacetophenone by whole cells of marine fungi.
The asymmetric reduction of 2-chloro-1-phenylethanone (1) by seven strains of marine fungi was evaluated and afforded (S)-(-)-2-chloro-1-phenylethanol with, in the best case, an enantiomeric excess of 50% and an isolated yield of 60%. The ability of marine fungi to catalyse the reduction was directly dependent on growth in artificial sea water-based medium containing a high concentration of Cl(-) (1.2 M). When fungi were grown in the absence of artificial sea water, no reduction of 1 by whole cells was observed. The biocatalytic reduction of 1 was more efficient at neutral rather than acidic pH values and in the absence of glucose as co-substrate.
Rocha
Lenilson C
LC
Instituto de Química de São Carlos, Universidade de São Paulo, Av. Trabalhador Sãocarlense, 400, CP 780, São Carlos, SP, CEP 13560-970, Brazil.
Ferreira
Hercules V
HV
Pimenta
Eli F
EF
Berlinck
Roberto G S
RG
Seleghim
Mirna H R
MH
Javaroti
Darci C D
DC
Sette
Lara D
LD
Bonugli
Rafaella C
RC
Porto
André L M
AL
D001711:Biotransformation; D003470:Culture Media / Q000737:chemistry; D005658:Fungi / Q000302:isolation & purification / Q000378:metabolism*; D010084:Oxidation-Reduction; D012623:Seawater / Q000382:microbiology*; D002721:omega-Chloroacetophenone / Q000378:metabolism*
D003470:Culture Media; D002721:omega-Chloroacetophenone