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- MakaleAçık Erişim2024Scopus SJRQ3Optimization of asymmetric bioreduction conditions of 1-indanone by Leuconostoc mesenteroides N6 using a face-centered design-based multi-objective optimization model
Alamoudi, Mohammed; Özdemir, Akın; Dertli, Enes; Bolubaid, Mohammed; Alidrisi, Hassan M.; Taylan, Osman; Yılmaz, Mustafa Tahsin; Şahin, Engin
There has been an increasing interest in biocatalysts over the past few decades in order to obtain high efficiency, high yield, and environmentally benign procedures aiming at the manufacture of pharmacologically relevant chemicals. Lactic Acid Bacteria (LAB), a microbial group, can be employed as biocatalysts while performing asymmetric reduction of prochiral ketones. In this study, Leuconostoc mesenteroides N6 was used for the asymmetric bioreduction 1-indanone. And then, a novel and innovative face-centered design-based multi-objective optimization model was used to optimize experimental conditions. Also, the experimental design factors were defined as agitation speed, incubation period, pH, and temperature for optimization to acquire the maximum enantiomeric excess (ee) and conversion rate (cr) values. When using the face-centered design-based multi-objective optimization model, the optimum culture conditions corresponded to 96.34 and 99.42%, ee and cr responses, respectively, were pH = 5.87, incubation temperature = 35 °C, incubation period = 50.88 h, and agitation speed = 152.60 rpm. Notably, the validation experiment under the optimum model conditions confirmed the model results. This study demonstrated the importance of the optimization and the efficiency of the face-centered design-based multi-objective model.
AtıfScopus1WoS9OpenAlex1
İncele - MakaleAçık Erişim2023Scopus SJRQ3Optimization of asymmetric bioreduction conditions of 1-(thiophen-2-yl)ethanone by Weissella cibaria N9 using a desirability function-embedded face-centered optimization model
Bolubaid, Mohammed; Özdemir, Akın; Dertli, Enes; Alamoudi, Mohammed; Taylan, Osman; Karaboğa, Derviş; Yılmaz, Mustafa Tahsin; Şahin, Engin
Prochiral ketones can be effectively bio-reduced to chiral secondary alcohols by whole-cell biocatalysts, which are possible useful precursors to synthesize physiologically active chemicals and natural products. When whole-cell biocatalysts strains are used, bioreduction process can be influenced by various cultural factors, and it is vital to optimize these factors that affect selectivity, conversion rate, and yield. In this study, Weissella cibaria N9 was used as whole-cell biocatalyst for bioreduction of 1-(thiophen-2-yl)ethanone, and cultural design factors were optimized using a desirability function-embedded face-centered optimization model. For this, effects of pH (4.5–5.5–6.5, x 1), (2) temperature (25–30–35 °C, x 2), (3) incubation period (24–48–72 h, x 3), and (4) agitation speed (100–150–200 rpm, x 4) on two response variables; (1) ee (%) and (2) cr (%) were tested. Next, desirability function-embedded face-centered optimization model revealed that a pH of 6.43, a temperature of 26.04 °C, an incubation period of 52.41 h, and an agitation speed of 150 rpm were the optimum levels and the estimated ee and cr responses were 99.31% and 98.16%, respectively. Importantly, the actual experimental ee and cr responses were similar to the estimated values indicating the capability of the offered desirability function-embedded face-centered optimization model when using the optimum cultural conditions.
AtıfScopus1WoS1OpenAlex3İncele - MakaleAçık Erişim2021Scopus SJRQ3Asymmetric reduction of prochiral aromatic and hetero aromatic ketones using whole-cell of Lactobacillus senmaizukei biocatalyst
Çolak, Nida Sezin; Kalay, Erbay; Şahin, Engin
Asymmetric bioreduction of aromatic and heteroaromatic ketones is an important process in the production of precursors of biologically active molecules. In this study, the bioreduction of aromatic and hetero aromatic prochiral ketones into optically active alcohols was investigated using Lactobacillus senmaizukei as a whole-cell catalyst, since whole-cells are less expensive than pure enzymes. The study indicates enantioselective bioreduction of various substituted aromatic ketones (1–16) to the corresponding (R)-and (S)-chiral secondary alcohols (1a–16a) in low to excellent enantioselectivity (6–94%) with good yields (58–95%). In addition, heteroaromatic prochiral ketones 1-(pyridin-2-yl)ethanone (17) and 1-(furan-2-yl)ethanone (18) were reduced to (R)-17a and (R)-18a in enantiopure form with excellent conversion (>99%) and yields. These findings show that L. senmaizukei is a very important biocatalyst for asymmetric reduction of both 6-membered and 5-member heteroaromatic methyl ketones. This method promising a green synthesis for the synthesis of biologically important secondary chiral alcohols in an environmentally friendly and inexpensive process.
AtıfScopus20WoS20OpenAlex19İncele - MakaleYalnız künye2020Scopus SJRQ4Green synthesis of chiral aromatic alcohols with Lactobacillus kefiri P2 as a novel biocatalyst
Baydaş, Yasemin; Dertli, Enes; Şahin, Engin
Biocatalytic reduction is a very important field of research in synthetic organic chemistry. Herein, three different Lactic Acid Bacteria (LAB) strains were evaluated for their bioreduction potential using acetophenone as a model substrate. Among these strains, Lactobacillus kefiri P2 strain was determined as the best asymmetric reduction biocatalyst. Reaction optimization parameters such as reaction time, temperature, agitation speed and pH were systematically optimized using Lactobacillus kefiri P2 strain and model substrate acetophenone. Under these optimized reaction conditions, secondary chiral alcohols were obtained by bioreduction of various prochiral ketones with results up to 99% enantiomeric excess. In addition, the steric and electronic effects of substituents on enantioselectivity and conversion were evaluated. It has been shown that Lactobacillus kefiri P2 biocatalyst was an effective catalyst for asymmetric reduction. This method provides an environmentally friendly method for the synthesis of optically pure alcohols and an alternative approach to chemical catalysts.
AtıfScopus24WoS22OpenAlex22İncele