Sürdürülebilir Kalkınma Amaçları
Yazarlar
- Şahin, Engin(6)
- Dertli, Enes(4)
- Taylan, Osman(2)
- Yilmaz, Mustafa Tahsin(2)
- Alamoudi, Rami(1)
- Bakhsh, Ahmed(1)
- Balubaid, Mohammed(1)
- Cebeci, Fatma(1)
- El-Obeid, Tahra(1)
- Herrera-Viedma, Enrique(1)
- Kalay, Erbay(1)
- Mayer, Melinda J.(1)
- Mithen, Richard(1)
- Narbad, Arjan(1)
- Rossiter, John T.(1)
- Serencam, Hüseyin(1)
- Tozlu, Caner(1)
- Çolak, Nida Sezin(1)
Yayınlar
- MakaleAçık Erişim2022Scopus SJRQ1Molecular Cloning, Expression and Characterisation of a Bacterial Myrosinase from Citrobacter Wye1
Cebeci, Fatma; Mayer, Melinda J.; Rossiter, John T.; Mithen, Richard; Narbad, Arjan
Glucosinolates are plant natural products which on degradation by myrosinases give rise to the beneficial bioactive isothiocyanates. Recently, a myrosinase activity was detected in a Citrobacter strain isolated from soil. This enzyme was purified enabling its amino acid sequence and gene sequence (cmyr) to be determined. In order to study this myrosinase it was necessary to establish an expression system that would enable future work such as a structural determination of the protein to be carried out. The myrosinase gene was amplified, cloned and expressed in Escherichia coli with a 6XHis-tag. The heterologous expression of cmyr enabled relatively large amounts of myrosinase to be produced (3.4 mg cmyr/100 ml culture). Myrosinase activity was determined by mixing substrate and enzyme and determining glucose release. Optimum pH and temperature were determined to be pH 6.0 and 25 °C for the Ni-NTA purified protein. The kinetic parameters of the purified myrosinase were determined using sinigrin as a substrate. Km and Vmax were estimated as 0.18 mM and 0.033 mmol/min/mg respectively for sinigrin under optimum conditions and compared to other kinetic data for myrosinases. The substrate specificity of myrosinase was determined having the highest affinity for sinigrin followed by glucoiberin, progoitrin, glucoerucin, glucoraphanin and glucotropaeolin.
AtıfScopus21WoS14OpenAlex16
İncele - MakaleYalnız künye2022Scopus SJRQ3Biocatalytic asymmetric synthesis of (S)-1-indanol using Lactobacillus paracasei BD71
Kalay, Erbay; Dertli, Enes; Şahin, Engin
Enantiopure benzo-fused cyclic alcohols have been used as a building block of a drug for Parkinson’s disease. Biocatalytic reduction of ketones is one of the most promising and significant routes to prepare optically active alcohols. In this study, the reductive capacity of seven lactic acid bacteria (LAB) strains were investigated as whole-cell biocatalyst in the enantioselective reduction of 1-indanone (1). Lactobacillus paracasei BD71 was found to have the best reductive capacity. Effects of different parameters such as pH, incubation time, agitation speed and temperature, on enantiomeric excess (ee) and conversion were investigated in a bioconversion. (S)-1-indanol ((S)-2) could be used as precursor for the synthesis of rasagiline mesylate TVP1012 for the therapy of Parkinson’s illness. It was produced in gram-scale (5.24 g), high yield (93%) and enantiomerically pure form using L. paracasei BD71 whole-cell biocatalysts. Also, to our knowledge, this is the first report on production of (S)-2 using whole-cell catalyst in enantiopure form, excellent yield, conversion and gram scale. This is a cheap, clean and eco-friendly process for production of (S)-2 compared to chemical processes.
AtıfScopus6WoS6OpenAlex6İncele - MakaleAçık Erişim2020MACHINE LEARNING APPLICATION FOR OPTIMIZING ASYMMETRICAL REDUCTION OF ACETOPHENONE EMPLOYING COMPLETE CELL OF LACTOBACILLUS SENMAIZUKE AS AN ENVIRONMENTALLY FRIENDLY APPROACH
Taylan, Osman; Yilmaz, Mustafa Tahsin; Balubaid, Mohammed; Alamoudi, Rami; El-Obeid, Tahra; Dertli, Enes; Şahin, Engin; Bakhsh, Ahmed; Herrera-Viedma, Enrique
Recently, optimization of the bioreduction reactions by optimization methodologies has gained special interest as these reactions are affected by several extrinsic factors that should be optimized for higher yields. An important example for these kinds of reactions is the complete cell implications for the bioreduction of prochiral ketones in which the culture parameters play crucial roles. Such biocatalysts provide environmentally friendly and clean methodology to perform reactions under mild conditions with high conversion rates. In the present work, at the first step the Lactobacillus senmaizuke was isolated from sourdough and the complete cell application of Lactobacillus senmaizuke for the bioreduction of acetophenone was optimized by an Artificial Neural networks (ANNs) to achieve the highest enantiomeric excess (EE, %). The culture parameters, pH, temperature, incubation period and agitation speed were the experimental factors that were optimized to maximize EE (%) by machine learning algorithm of Artificial Intelligence modeling and the best conditions to maximize EE (95.5 %) were calculated to be pH of 5.7, temperature of 35 ºC, incubation period of 76 h and agitation speed of 240 rpm with very low sum of squared error value (0.611236 %) to bioreduce acetophenone using complete cell of Lactobacillus senmaizuke as a sourdough isolate GRAS microbial species. Accordingly, The ANN was employed to correctly establish the enantiomeric excess values of the specimen with an average absolute error 0.080739 %.
AtıfScopus3WoS2OpenAlex2İncele - MakaleYalnız künye2020Scopus SJRQ4Production of enantiopure chiral aryl heteroaryl carbinols using whole‐cell Lactobacillus paracasei biotransformation
Şahin, Engin
Aryl and heteroaryl chiral carbinols are useful precursors in the synthesis of drugs. Lactobacillus paracasei BD87E6, which is obtained from a cereal based fermented beverage, was investigated as whole cell biocatalyst for the bioreduction of different ketones (including aromatic, hetero-aromatic and fused bicyclic ketone) into chiral carbinols, which can be used as a pharmaceutical intermediate. The study shows that bioreduction of aryl, heteroaryl and fused bicyclic ketone (1–5) to their corresponding chiral carbinols (1a–5a) in excellent enantioselectivity (>99%) with high yields. This study gave the first example for an enantiopure production of (S)-6-chlorochroman-4-ol (3a), which has many antioxidant activity, by a biological method. For asymmetric bioreduction of other prochiral ketones, these results open way to use of L. paracasei BD87E6 as biocatalysts. Also, the present process shows a hopeful and alternative green synthesis for the production of enantiopure carbinols in a mild, inexpensive and environmentally friendly process.
AtıfScopus21WoS18OpenAlex20İncele - MakaleAçık Erişim2020Scopus SJRQ3Synthesis of enantiopure (S)-6-chlorochroman-4-ol using whole-cell Lactobacillus paracasei biotransformation
Şahin, Engin
Chromane, which has a fused cyclic structure, is a significant molecule that can be found in the structure of many important compounds. Lactobacillus paracasei BD101 was demonstrated as whole-cell biocatalyst for the synthesis of (S)-6-chlorochroman-4-ol with immense enantioselectivity. The conditions of asymmetric reduction were optimized one factor by one factor using L paracasei BD101 to achieve enantiomerically pure product and complete conversion. Using these obtained optimization conditions, asymmetric reduction of 6-chlorochroman-4-one was performed under environmentally friendly conditions; 6-chlorochroman-4-one, having a fused cyclic structure as previously noted to be difficult to asymmetric reduction with biocatalysts, was enantiomerically reduced to (S)-6-chlorochroman-4-ol with an enantiomeric excess >99% on a high gram scale. This study is the first example in the literature for the enantiopure synthesis of (S)-6-chlorochroman-4-ol using a biocatalyst. Also notably, the optical purity of (S)-6-chlorochroman-4-ol obtained in this study through asymmetric bioreduction using whole-cell biocatalyst is the highest value in the literature. In this study, (S)-6-chlorochroman-4-ol was produced on a gram scale by an easy, inexpensive, and environmentally friendly method, which has shown the production of valuable chiral precursors for drug synthesis and other industrial applications. This study provides a convenient method for the production of (S)-6-chlorochroman-4-ol, which can meet the industrial green production demand of this chiral secondary alcohol.
AtıfScopus23WoS23OpenAlex24İncele - MakaleYalnız künye2019Scopus SJRQ3Response surface methodology as optimization strategy for asymmetric bioreduction of acetophenone using whole cell of Lactobacillus senmaizukei
Çolak, Nida Sezin; Şahin, Engin; Dertli, Enes; Yilmaz, Mustafa Tahsin; Taylan, Osman
Whole cell applications are one of the main methodologies for the bioreduction of prochiral ketones to obtain enantiomerically rich chiral secondary alcohols which are mainly affected by the culture parameters of the whole cell. In this study, whole cell of Lactobacillus senmaizukei as a safe Lactic Acid Bacteria (LAB) was used for the reduction of acetophenone and Response Surface Methodology (RSM) application was used to optimize the culture parameters in terms of temperature, pH, incubation time, and agitation level to obtain the highest enantiomeric excess (ee) and conversion rate. The predicted optimum conditions for the bioreduction with whole cell Lactobacillus senmaizukei were found to be pH of 5.25, temperature of 25 °C, incubation time of 72 hr, and agitation level of 100 rpm. Importantly, the efficiency of the reduction of the acetophenone was significantly affected by the linear and quadratic effects of culture parameters. These findings are important to show the role of culture parameters for the bioreduction reactions and also the efficiency of the RSM technique to optimize these parameters.
AtıfScopus10WoS10OpenAlex11İncele - MakaleYalnız künye2019Scopus SJRQ3Production of enantiomerically enriched chiral carbinols using Weissella paramesenteroides as a novel whole cell biocatalyst
Tozlu, Caner; Şahin, Engin; Serencam, Hüseyin; Dertli, Enes
In this study, four bacterial strains were tested for their ability to reduce acetophenones to its corresponding alcohol. Among these strains Weissella paramesenteroides N7 was found to be the most successful biocatalyst to reduce the ketones to the corresponding alcohols. The reaction conditions were systematically optimized for W. paramesenteroides N7 that resulted in high enantioselectivity and conversion rates for the bioreduction. The scale-up asymmetric reduction of 1-(4-methoxyphenyl) propan-1-one (1r) by W. paramesenteroides N7 gave (R)-1-(4-methoxyphenyl) propan-1-ol (2r) with 94% yield and >99% enantiomeric excess. This is the first report showing the synthesis of (R)-1-(4-methoxyphenyl) propan-1-ol (2r) in enantiopure form using a biocatalyst on a gram scale. The whole cell catalyzed the reductions of ketone substrates on the preparative scale, demonstrating that W. paramesenteroides N7 would be a valuable biocatalyst for the preparation of chiral aromatic alcohols of pharmaceutical interest as a promising and alternative green approach.
AtıfScopus12WoS10OpenAlex11İncele