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Öğe Asymmetric reduction of aromatic heterocyclic ketones with bio-based catalyst Lactobacillus kefiri P2(Springer International Publishing Ag, 2021) Baydas, Yasemin; Kalay, Erbay; Sahin, EnginChiral heterocyclic secondary alcohols have received much attention due to their widespread use in pharmaceutical intermediates. In this study, Lactobacillus kefiri P2 biocatalysts isolated from traditional dairy products, were used to catalyze the asymmetric reduction of prochiral ketones to chiral secondary alcohols. Secondary chiral carbinols were obtained by asymmetric bioreduction of different prochiral substrates with results up to>99% enantiomeric excess (ee). (R)-1-(benzofuran-2-yl)ethanol 5a, which can be used in the synthesis of pharmaceuticals such as bufuralols potent nonselective beta-blockers antagonists, Amiodarone (cardiac anti-arrhythmic), and Benziodarone (coronary vasodilator), was produced in gram-scale, high yield and enantiomerically pure form using L. kefiri P2 biocatalysts. The gram-scale production was carried out, and 9.70 g of (R)-5a in enantiomerically pure form was obtained in 96% yield. Also, production of (R)-5a in terms of yield and gram scale through catalytic asymmetric reduction using the biocatalyst was the highest report so far. This is a cost-effective, clean and eco-friendly process for the preparation of chiral secondary alcohols compared to chemical processes. From an environmental and economic perspective, this biocatalytic method has great application potential, making it a green and sustainable way of synthesis.Öğe Asymmetric reduction of prochiral aromatic and hetero aromatic ketones using whole-cell of Lactobacillus senmaizukei biocatalyst(Taylor & Francis Inc, 2021) Colak, Nida Sezin; Kalay, Erbay; Sahin, EnginAsymmetric 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.Öğe Bio-catalytic asymmetric synthesis of ?-adrenergic receptor blocker precursor: (R)-2-bromo-1-(naphthalen-2-yl)ethanol(Taylor & Francis Ltd, 2020) Tasdemir, Volkan; Kalay, Erbay; Dertli, Enes; Sahin, EnginAromatic alpha-halohydrins, particularly 2-haloethanols as significant precursor of drugs, can easily be converted to chiral beta-adrenergic receptor blockers. Eight strains of Lactobacillus curvatus were tested as biocatalysts for asymmetric reduction of 2-bromo-1-(naphthalen-2-yl)ethanone 1 to 2-bromo-1- (naphthalen-2-yl) ethanol 2. The parameters of the bioreduction were optimized using L. curvatus N4, the best biocatalyst found. As a result, (R)-2-bromo-1-(naphthalen-2-yl)ethanol 2, which can be beta-adrenergic receptor blocker precursor, was produced for the first time in high yield and enantiomerically pure form using biocatalysts. Moreover, the gram scale synthesis was performed and 7.54 g of (R)-2 was synthesized as enantiopure form (enantiomeric excess >99%) in 48 h. The important advantages of this process are that it produces of (R)-2 for the first time in enantiopure form, in excellent yield and under environmentally friendly and moderate reaction conditions. This system is of the potential to be applied at a commercial scale.Öğe Biocatalytic asymmetric synthesis of (R)-1-tetralol using Lactobacillus paracasei BD101(Wiley, 2021) Kalay, Erbay; Sahin, EnginAsymmetric bioreduction of ketones is a fundamental process in the production of organic molecules. Compounds containing tetralone rings are found in the structure of many biologically active and pharmaceutical molecules. 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 Lactobacillus paracasei BD101 was investigated as whole-cell biocatalyst in the enantioselective reduction of 1-tetralone (1). In biocatalytic reduction reactions, the conversion of the substrate and the enantiomeric excess (ee) of the product are significantly affected by optimization parameters such as temperature, agitation rate, pH, and incubation time. Effects of these parameters on ee and conversion were investigated comprehensively. (R)-1-tetralol ((R)-2), which can be used to treat disorder such as obsessive compulsive, post-traumatic stress, premenstrual dysphoric, and social anxiety, was manufactured in enantiopure form, high yield and gram-scale, using whole-cell biocatalysts of L. paracasei BD101. The 7.04 g of (R)-2 was obtained in optically pure form with 95% yield. Also, to our knowledge, this is the first report on production of (R)-2 using whole-cell biocatalyst in excellent yield, conversion, enantiopure form and gram scale. This is a clean, eco-friendly and cheap method for the synthesis of (R)-2 compared with chemical catalyst.Öğe Biocatalytic asymmetric synthesis of (S)-1-indanol using Lactobacillus paracasei BD71(Taylor & Francis Ltd, 2022) Kalay, Erbay; Dertli, Enes; Sahin, EnginEnantiopure 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.Öğe Design, synthesis, antioxidant and anticholinesterase activities of novel isonicotinic hydrazide-hydrazone derivatives(Elsevier, 2023) Aslanhan, Ozlem; Kalay, Erbay; Tokali, Feyzi Sinan; Can, Zehra; Sahin, EnginThe design and synthesis of hydrazone derivatives are increasing in popularity day by day due to the significant biological activities of this scaffold. In the present study, twelve novel isonicotinic hydrazide-hydrazone analogues were synthesized by the condensation reaction of isonicotinic hydrazide with ben-zaldehyde possessing sulfonate moiety. The structures of the novel compounds have been characterized in detail using spectroscopic techniques. All compounds have shown inhibitory effects against the AChE en-zyme at rates ranging from 21.00 to 59.48%. Among them, compound 5 has exhibited the best inhibitory effect of 59.48% against AChE at a concentration of 0.1 mM. Furthermore, to determine how effective the novel compounds are as antioxidants, FRAP and DPPH studies were also carried out. FRAP values in compounds 1-12 were found to range from 26.989-3415.556 mu mol FeSO4.7H2O/mg. They also displayed moderate antioxidant potential in the range of SC50= 0.03-87.32 mg/mL compared with the control Trolox (SC50 = 0.004) in DPPH radical scavenging activities. It was seen that the AChE inhibition percentages of the compounds were in the range of 23.04-58.10% at 0.1 mM concentration. This is the first research on the synthesis, antioxidant and enzyme inhibition properties of these compounds. (c) 2023 Elsevier B.V. All rights reserved.Öğe Production of enantiomerically enriched chiral carbinols using whole-cell biocatalyst(Taylor & Francis Ltd, 2022) Baydas, Yasemin; Kalay, Erbay; Sahin, EnginBiocatalytic asymmetric reduction of ketone is an efficient method for the production of chiral carbinols. The study indicates selective bioreduction of different ketones (1-8) to their respective (R)-alcohols (1a-8a) in low to high selectivity (0- >99%) with good yields (11-96%). In this work, whole-cell of Lactobacillus kefiri P2 catalysed enantioselective reduction of various prochiral ketones was investigated. (R)-4-Phenyl-2-butanol 2a, which is used as a precursor to antihypertensive agents and spasmolytics (anti-epileptic agents), was obtained using L kefiri P2 in 99% conversion and 91% enantiomeric excess (ee). Moreover, bioreduction of 2-methyl-1-phenylpropan-1-one substrate 8, containing a branched alkyl chain and difficult to asymmetric reduction with chemical catalysts as an enantioselective, to (R)-2-methyl-1-phenylpropan-1-ol (8a) in enantiomerically pure form was carried out in excellent yield (96%). The gram-scale production was carried out, and 9.70 g of (R)-2-methyl-1-phenylpropan-1-ol (8a) in enantiomerically pure form was obtained in 96% yield. Also especially, the yield and gram scale of (R)-2-methyl-1-phenylpropan-1-ol (8a) synthesised through catalytic asymmetric reduction using the biocatalyst was the highest report so far. The efficiency of L kefiri P2 for the conversion of the substrates and ee of products were markedly influenced by the steric factors of the substrates. This is a cheap, clean and eco-friendly process for production of chiral carbinols compared to chemical processes.Öğe Regioselective asymmetric bioreduction of trans-4-phenylbut-3-en-2-one by whole-cell of Weissella cibaria N9 biocatalyst(Wiley, 2021) Kalay, Erbay; Sahin, EnginThere is a considerable interest in the asymmetric production of chiral allylic alcohols, the main building blocks of many functional molecules. The asymmetric reduction of alpha,beta-unsaturated ketones is difficult with traditional chemical protocols in a regioselective and stereoselective manner. In this study, the reductive capacity of whole cell of Leuconostoc mesenteroides N6, Weissella paramesenteroides N7, Weissella cibaria N9, and Leuconostoc pseudomesenteroides N13 was investigated as whole-cell biocatalysts in the enantioselective reduction of (E)-4-phenylbut-3-en-2-one (1). The biocatalytic reduction of 1 to (S,E)-4-phenylbut-3-en-2-ol ((S,E)-2) using the whole cell of W. cibaria N9 isolated from Turkish sourdough was developed in a regioselective fashion, occurring with excellent conversion and recovering the product in good yield. In biocatalytic reduction reactions, the conversion of the substrate and the enantiomeric excess (ee) of the product are significantly affected by optimization parameters such as temperature, agitation rate, pH, and incubation time. Effects of these parameters on ee and conversion were investigated comprehensively. In addition, to our knowledge, this is the first report on production of (S,E)-2 using whole-cell biocatalyst in excellent yield, conversion with enantiopure form and at gram scale. These findings pave the way for the use of whole cell of W. cibaria N9 for challenging higher substrate concentrations of different alpha,beta-unsaturated ketones for regioselective reduction at industrial scale.Öğe Synthesis of Arylsulfonyl Hydrazone Derivatives: Antioxidant Activity, Acetylcholinesterase Inhibition Properties, and Molecular Docking Study(Wiley-V C H Verlag Gmbh, 2023) Demirci, Yasin; Kalay, Erbay; Kara, Yakup; Guler, Halil Ibrahim; Can, Zehra; Sahin, EnginIn this current paper, fifteen novel sulfonyl hydrazone derivatives have been successfully synthesized and evaluated for antioxidant activity as well as their effects on inhibitory activity toward acetylcholinesterase (AChE). By using H-1 NMR, C-13 NMR, FT-IR, and high-resolution mass spectrometry methods, the full characterization data of the novel compounds were obtained. The synthesized compounds capacity to inhibition glucosidase and exhibit antioxidant activity were tested in vitro. It was determined that compounds (E)-4-((2-((4-chlorophenyl)sulfonyl)hydrazone)methyl)-2-methoxyphenylfuran-2-carboxylate (21), (E)-2-methoxy-4-((2-(phenylsulfonyl)hydrazone)methyl)phenylfuran-2-carboxylate (17) and (E)-4-((2-((4-bromophenyl)sulfonyl)hydrazone)methyl)-2-methoxyphenylfuran-2-carboxylate (25) showed good antioxidant activity. Upon examining the acetylcholinesterase inhibitory activity, it was determined that compounds (E)-2-methoxy-4-((2-((4-methoxyphenyl)sulfonyl) hydrazone)methyl)phenylacetate (27) (10.39 & mu;M), (E)-4-((2-((4-chloro phenyl)sulfonyl) hydrazone)methyl)-2-methoxyphenylfuran-2-carboxylate (21) (10.81 & mu;M), (E)-4-((2-((4-chloro phenyl)sulfonyl)hydrazone)methyl)-2-methoxyphenyl thiophene-2-carboxylate (22) (12.92 & mu;M) and (E)-2-methoxy-4-((2-(phenylsulfonyl)hydrazone)methyl)phenylfuran-2-carboxylate (17) (12.93 & mu;M) showed potent inhibitory effects. Molecular docking simulations were used to investigate the interactions of novel sulfonyl hydrazone derivatives with human acetylcholinesterase protein. The ligands exhibited strong binding to the receptor protein with potent inhibition.
