Production of (S)-2`-fluorophenylethan-1-ol and (S)-3`- fluorophenylethan-1-ol by Alternaria alternata using ram horn peptone in microbial growth medium

Authors : Esabi Başaran KURBANOĞLU, , Namudar İzzet KURBANOĞLU, Kani ZILBEYAZ

Pages : 39-46

View : 14 | Download : 7

Publication Date : 2010-12-01

Article Type : Research Paper

Abstract :Enantiomerically pure, fluorinated compounds have an important role in medicinal chemistry. Alternaria alternata isolates were used for the synthesis of insert ignore into journalissuearticles values(S);-2`-fluorophenylethan-1-ol 1b and insert ignore into journalissuearticles values(S);-3`-fluorophenylethan-1-ol 2b. Biocatalytic syntheses of optically active 1b and 2b were achieved by asymmetric reduction of 2`-fluoroacetophenone 1a and 3`-fluoroacetophenone 2a in the batch culture of A. alternata containing ram horn peptone insert ignore into journalissuearticles values(RHP);. The reaction conditions insert ignore into journalissuearticles values(pH, temperature, and agitation); that improve the conversion of the substrates were studied. The optimal reaction conditions were found as pH 6.0, agitation 250, temperature 32 °C and substrate 3 mmol/100 mL. The gram scale productions of 1b and 2b by the most effective biocatalyst A. alternata EBK-6 using RHP was carried out in a fermenter with 1-L working volume. The results showed that the yields with >99% enantiomeric excess insert ignore into journalissuearticles values(ee); of both 1b and 2b reached 75% for 1b and 66% for 2b. The concentrations of products 1b and 2b at the end of fermentation were 3.1 g/L and 2.8 g/L, respectively. As a result, 2 important chiral intermediates for the pharmaceutical industry using A. alternata EBK-6 in the submerged culture containing RHP from waste material were scaled up to gram scale with excellent ee.
Keywords : Key words Alternaria alternata, bioconversion, fluoroacetophenone, fermentation, ram horn, optimization