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- MakaleAçık Erişim2022Scopus SJRQ1Optimization of Asymmetric Bioreduction Conditions of 2-methyl-1-phenylpropan-1-one by Lactobacillus fermentum BY35 Using I-Optimal Design-Based Model
Aksuoğlu, Selmani; Özdemir, Akın; Serencam, Hüseyin; Dertli, Enes; Şahin, Engin
The bioreduction of prochiral ketones offers efficient access to chiral secondary alcohols, which are potentially beneficial precursors for producing many biologically active compounds and natural products. This bioreduction process can be affected by different parameters when whole-cell of biocatalysts such as Lactic Acid Bacteria strains are applied. In this context, this paper proposed an I-optimal design-based model to optimize culture parameters such as temperature, pH, incubation period, and agitation speed for asymmetric bioreduction of 2-methyl-1-phenylpropan-1-one (1) with Lactobacillus fermentum BY35 as a biocatalyst while achieving the highest conversion rate (cr) and enantiomeric excess (ee). The optimum settings of the four culture parameters and the cr and ee values were found using the proposed optimization model as follows: pH = 6.5, temperature = 25 °C, incubation period = 38.5 h, agitation speed = 200 rpm, the ee value = 98.78%, and the cr value = 98.92%. After the validation of the process, the cr and ee values were found to be > 99% and > 99%, respectively, while using the optimum operating conditions from the optimization model. Thus, the results of the optimization model are consistent with the results of the validation experiment. It is also noted that this paper is the first to optimize culture parameters using the proposed I-optimal design-based model for an asymmetric reduction.
AtıfScopus3WoS3OpenAlex3
İncele - MakaleAçık Erişim2019Scopus SJRQ3Whole cell application of Lactobacillus paracasei BD101 to produce enantiomerically pure (S)-cyclohexyl(phenyl)methanol
Şahin, Engin; Serencam, Hüseyin; Dertli, Enes
In this study, a total of 10 bacterial strains were screened for their ability to reduce cyclohexyl(phenyl)methanone 1 to its corresponding alcohol. Among these strains, Lactobacillus paracasei BD101 was found to be the most successful biocatalyst to reduce the ketones to the corresponding alcohols. The reaction conditions were systematically optimized for the reducing agent L paracasei BD101, which showed high enantioselectivity and conversion for the bioreduction. The preparative scale asymmetric reduction of cyclohexyl(phenyl)methanone (1) by L paracasei BD101 gave (S)-cyclohexyl(phenyl)methanol (2) with 92% yield and >99% enantiomeric excess. The preparative scale study was carried out, and a total of 5.602 g of (S)-cyclohexyl(phenyl)methanol in high enantiomerically pure form (>99% enantiomeric excess) was produced. L paracasei BD101 has been shown to be an important biocatalyst in asymmetric reduction of bulky substrates. This study demonstrates the first example of the effective synthesis of (S)-cyclohexyl(phenyl)methanol by the L paracasei BD101 as a biocatalyst in preparative scale.
AtıfScopus39WoS37
İncele - MakaleAçık Erişim2018Scopus SJRQ2Production of (R)-1-(1,3-benzodioxol-5-yl)ethanol in high enantiomeric purity by Lactobacillus paracasei BD101
Şahin, Engin
Piperonyl ring is found in a number of naturally occurring compounds and possesses enormous biological activities. There are many studies in the literature with compounds containing a piperonyl ring, but there are very few studies on the synthesis of chiral piperonyl carbinol. The objective of this study was to determine the microbial reduction ability of bacterial strains and to reveal the effects of different physicochemical parameters on this reduction ability. A total of 15 bacterial isolates were screened for their ability to reduce 1-(benzo[d][1,3]dioxol-5-yl) ethanone 1 to its corresponding alcohol. Among these isolates Lactobacillus paracasei BD101 was found to be the most successful biocatalyst to reduce the ketone containing piperonyl ring to the corresponding alcohol. The reaction conditions were systematically optimized for the reducing agent L paracasei BD101, which showed high enantioselectivity and conversion for the bioreduction. The preparative scale study was performed, and a total of 3.72 g of (R)-1-(1,3-benzodioxol-5-yl) ethanol in high enantiomeric form (>99% enantiomeric excess) was produced in a mild, cheap, and environment-friendly process. This study demonstrates that L paracasei BD101 can be used as a biocatalyst to obtain chiral carbinol with excellent yield and selectivity.
AtıfScopus43WoS42İncele - MakaleAçık Erişim2017Scopus SJRQ2Highly Enantioselective Production of Chiral Secondary Alcohols with Candida zeylanoides as a New Whole Cell Biocatalyst
Şahin, Engin; Dertli, Enes
The increasing demand for biocatalysts in synthesizing enantiomerically pure chiral alcohols results from the outstanding characteristics of biocatalysts in reaction, economic, and ecological issues. Herein, fifteen yeast strains belonging to three food originated yeast species Candida zeylanoides, Pichia fermentans, and Saccharomyces uvarum were tested for their capability for asymmetric reduction of acetophenone to 1-phenylethanol as biocatalysts. Of these strains, C. zeylanoides P1 showed an effective asymmetric reduction ability. Under optimized conditions, substituted acetophenones were converted to corresponding optically active secondary alcohols in up to 99% enantiomeric excess and at high yields. The preparative scale asymmetric bioreduction of 4-nitroacetophenone (1m) by C. zeylanoides P1 gave (S)-1-(4-nitrophenyl)ethanol (2m) with 89% yield and > 99% enantiomeric excess. Compound 2m has been obtained in an enantiomerically pure and inexpensive form. Additionally, these results indicate that C. zeylanoides P1 is a promising biocatalyst for the synthesis of chiral alcohols in industry.
AtıfScopus32WoS30İncele