RESUMEN
Ninety isolates of microorganisms belonging to different taxonomical groups (30 bacteria, 20 yeast, and 40 fungi) were previously isolated from various samples. These isolates were screened as reducing agents for acetophenone 1a to phenylethanol 2a. It was found that the isolate EBK-10 was the most effective biocatalyst for the enantioselective bioreduction of acetophenone. This isolate was identified as Rhodotorula glutinis by the VITEK 2 Compact system. The various parameters (pH 6.5, temperature 32 degrees C, and agitation 200 rpm) of the bioreduction reaction was optimized, which resulted in conversions up to 100% with >99% enantiomeric excesses (ee) of the S-configuration. The preparative scale bioreduction of acetophenone 1a by R. glutinis EBK-10 gave (S)-1-phenylethanol 2a in 79% yield, complete conversion, and >99% ee. In addition, R.glutinis EBK-10 successfully reduced various substituted acetophenones.
Asunto(s)
Acetofenonas/química , Acetofenonas/metabolismo , Rhodotorula/aislamiento & purificación , Rhodotorula/metabolismo , Alcoholes/química , Alcoholes/metabolismo , Biocatálisis , Cromatografía Líquida de Alta Presión , Oxidación-Reducción , EstereoisomerismoRESUMEN
The asymmetric reductions of acetophenone and its analogues using once immobilized Rhodotorula glutinis cells were studied. The performance and reaction parameters of the immobilized cells were also investigated and it was determined that the cells could be used 15 times in batch processes. All chiral alcohols obtained using purification procedures were of sufficient enantiopurity (>99%) of the (S)-enantiomer. The applicability of the optimized process for a preparative scale bioreduction was shown. Under the optimum conditions, 35mM (4.3g) of the product ((S)-1-phenylethanol) was produced from 45mM (5.4g) of the substrate (acetophenone) with one time immobilized R. glutinis EBK-2 cells (6g wet weight). The yield was calculated as 77%. In this study, it was found that the buffer level had a very significant effect on the reaction activity. Our results demonstrate that the optimized process can be implemented on a preparative scale.
Asunto(s)
Acetofenonas/metabolismo , Rhodotorula/metabolismo , Acetofenonas/química , Biomasa , Cromatografía Líquida de Alta Presión , Concentración de Iones de Hidrógeno , Cinética , Espectroscopía de Resonancia Magnética , Oxidación-Reducción , Rhodotorula/citología , TemperaturaRESUMEN
A total of 120 fungal strains were isolated from soil samples and evaluated in the bioreduction of substituted acetophenones to the corresponding (R)-alcohols. Among these strains, isolate Trichothecium roseum EBK-18 was highly effective in the production of (R)-alcohols with excellent enantioselectivity (ee > 99%). Gram scale preparation of (R)-1-phenylethanol is reported.
Asunto(s)
Acetofenonas/metabolismo , Hypocreales/aislamiento & purificación , Hypocreales/metabolismo , Alcohol Feniletílico/química , Alcohol Feniletílico/metabolismo , Oxidación-Reducción , Microbiología del Suelo , Estereoisomerismo , Especificidad por SustratoRESUMEN
Aspergillus niger EBK-9 was isolated from soil sample. This isolate was evaluated for production of (R)-1-(4-Bromo-phenyl)-ethanol 2 from 1-(4-Bromo-phenyl)-ethanone 1. In this work, the production of the 2 was achieved via fermenter. Glucose, yeast extract and ram horn peptone as medium in fermenter for growth of A. niger was used. A. niger EBK-9 isolate was found to be an effective biocatalyst with excellent enantiomeric excess (>99%) and good conversion (100%) for the production of the 2 in batch culture. The 8.2 mmol/l product from 10 mmol substrate under the optimum conditions could be produced. The yield was calculated as 82%. Because of the easy availability of the fungus besides simple reaction conditions, this process and medium must be potentially useful for production of chiral alcohols.
Asunto(s)
Aspergillus niger/metabolismo , Biotecnología/métodos , Peptonas/química , Alcohol Feniletílico/análogos & derivados , Alcoholes/química , Animales , Reactores Biológicos , Fermentación , Glucosa/metabolismo , Cuernos , Concentración de Iones de Hidrógeno , Modelos Químicos , Alcohol Feniletílico/química , Ovinos , Suelo , Factores de TiempoRESUMEN
The present study deals with the production of citric acid from a ram horn peptone (RHP) by Aspergillus niger NRRL 330. A medium from RHP and a control medium (CM) were compared for citric acid production using A. niger in a batch culture. For this purpose, first, RHP was produced. Ram horns were hydrolyzed by treatment with acids (6 N H(2)SO(4), 6 N HCl) and neutralizing solutions. The amounts of protein, nitrogen, ash, some minerals, total sugars, total lipids and amino acids of the RHP were determined. RHP was compared with peptones with a bacto-tryptone from casein and other peptones. The results from RHP were similar to those of standard peptones. The optimal concentration of RHP for the production of citric acid was found to be 4% (w/w). A medium prepared from 4% RHP was termed ram horn peptone medium (RHPM). In comparison with CM, the content of citric acid in RHPM broth (84 g/l) over 6 days was 35% higher than that in CM broth (62 g/l). These results show that citric acid can be produced efficiently by A. niger from ram horn.