Sürdürülebilir Kalkınma Amaçları

• 2

• MakaleAçık Erişim2022Scopus SJRQ3/r/bayburt/13478
  Optimization of lactose derivative hetero-oligosaccharides production using whey as the acceptor molecule by an active glucansucrase

  Kabli, Mohammad; İspirli, Hümeyra; Balubaid, Mohammed; Taylan, Osman; Yılmaz, Mustafa Tahsin; Dertli, Enes

  Glucansucrases are capable of synthesis of distinct oligosaccharides using different acceptor molecules and in this study lactose derivative hetero-oligosaccharides were shown to be produced by an active glucansucrase in its acceptor reaction with sucrose and whey as the donor-acceptor molecules, respectively. Following the monitoring of the reaction products by TLC analysis, the effects of reaction parameters in terms of enzyme concentration, sucrose/whey ratio and reaction temperature on final oligosaccharide yields (OY) were optimized by Response Surface Methodology (RSM). Results indicated that increment of enzyme concentration and reaction temperature decreased the OY in a particular reaction time whereas the OY increased with the increment of sucrose/whey ratio in the acceptor reactions of glucansucrase E81 with whey as the acceptor molecule. A low level of glucansucrase E81 concentration was sufficient to obtain the highest OY in the tested conditions. These findings demonstrated the importance of the optimisation of the reaction parameters for the acceptor reactions of the glucansucrases.

  AtıfScopus2·WoS4·OpenAlex6

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• MakaleAçık Erişim2022Scopus SJRQ3/r/bayburt/13332
  Production of enantiomerically enriched chiral carbinols using whole-cell biocatalyst

  Baydaş, Yasemin; Kalay, Erbay; Şahin, Engin

  Biocatalytic 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.

  AtıfScopus5·WoS5·OpenAlex6

  İncele
• MakaleYalnız künye2022Scopus SJRQ3/r/bayburt/12031
  Biocatalytic 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.

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  AtıfScopus6·WoS6·OpenAlex6

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• MakaleYalnız künye2020Scopus SJRQ3/r/bayburt/13455
  Production of mannose-containing oligosaccharides by glucansucrase E81 and determination of their functional characteristics

  İspirli, Hümeyra; Dertli, Enes

  Oligosaccharides are one of the functional ingredients to be used in food technology. In this study, by using an active glucansucrase GTFA-ΔN E81 in the acceptor reaction of mannose, mannose-containing oligosaccharides were produced and their functionality was tested. The formation of the oligosaccharides were visualised by TLC analysis and mannose-containing oligosaccharides up to DP 7 were determined by LC-MS analysis. The presence of the (1,6)Glc and (1,3)Glc units within the oligosaccharides were determined by NMR analysis. The in vitro immune-modulatory functions of the mannose-containing oligosaccharides were determined but no induction in IL-4, IL-10, IL-12 and TNF-α cytokine levels were detected. Importantly this oligosaccharide mixture showed prebiotic effect by triggering the growth of tested probiotics and not affecting the growth of pathogen strains. Our findings reveals the potential of the role of glucansucrases for the production of functional oligosaccharides.

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  AtıfScopus8·WoS7·OpenAlex8

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• MakaleAçık Erişim2020Scopus SJRQ3/r/bayburt/13289
  Bio-catalytic asymmetric synthesis of β-adrenergic receptor blocker precursor: (R)-2-bromo-1-(naphthalen-2-yl)ethanol

  Taşdemir, Volkan; Kalay, Erbay; Dertli, Enes; Şahin, Engin

  Aromatic α-halohydrins, particularly 2-haloethanols as significant precursor of drugs, can easily be converted to chiral β-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 β-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.

  AtıfScopus2·WoS2·OpenAlex2

  İncele
• MakaleYalnız künye2020Scopus SJRQ3/r/bayburt/12078
  First green synthesis of (R)-2-methyl-1-phenylpropan-1-ol using whole-cell Lactobacillus paracasei BD101 biotransformation

  Şahin, Engin

  Green chemistry includes a novel process in the production of drugs precursors and biological active molecules using biocatalysts, so reducing the threats for human sanitary and ecological pollutions. Asymmetric bioreduction of prochiral ketones by biocatalysts is one of the best prevalent used methods in synthetic organic chemistry due to the production of enantiopure chiral carbinols. This study emphasizes the application biocatalyst L paracasei BD101 for enantioselective bioreduction of 2-methyl-1-phenylpropan-1-one ketone, which contain branched alkyl chain, to (R)-2-methyl-1-phenylpropan-1-ol ((R)-2) in high yields and excellent enantiomeric excess (>99%). The scale-up production was performed, and 4.61 g of (R)-2 in enantiopure form was synthesized. L paracasei BD101 was proved to be a substantial biocatalyst in asymmetric bioreduction of a ketone which contains a branched alkyl chain. There is not any work in the literature similar to our study. Hence, it is important to work on filling this gap. This study is the first example for an enantiopure synthesis of (R)-2 by a biocatalyst. The new green method was developed for bioreduction of bulky ketones, which contains a branched alkyl chain, and it approves the synthesis of novel chiral carbinols in an easy, cheap, and environmentally friendly condition using L paracasei BD101.

  AtıfScopus10·WoS9·OpenAlex10

  İncele
• MakaleAçık Erişim2019Scopus SJRQ3/r/bayburt/13584
  Characterization of a glucansucrase from Lactobacillus reuteri E81 and production of malto-oligosaccharides

  İspirli, Hümeyra; Yüzer, Mustafa Onur; Skory, Christopher; Colquhoun, Ian J.; Sağdıç, Osman; Dertli, Enes

  Glucansucrases, which can be produced by different Lactic Acid Bacteria (LAB), catalyze the synthesis of α-glucans with different structures and properties using sucrose as substrate. In this study, a novel glucansucrase (GTFA) from Lactobacillus reuteri E81 was identified and heterologously expressed. Alignments of GTFA with other glucansucrases revealed its novelty and a putative 3D model structure was obtained. The biochemical properties of the truncated enzyme without the N-terminal variable region, GTFA-ΔN, was characterized. The Km and Vmax were found to be 7.5 mM and 1.49 IU/mg, respectively, and it showed optimum activities at pH 7 and at 50 °C. The GTFA-ΔN produced in vitro an α-glucan with (α1 → 3) and (α1 → 6) glycosidic linkages using sucrose as the substrate. Importantly, GTFA-ΔN synthesized DP = 9 oligosaccharides using sucrose and maltose as the donor and acceptor sugars, respectively, as detected by TLC, HPLC, LC-MS and NMR analysis.

  AtıfScopus40·WoS40·OpenAlex40

  İncele
• MakaleAçık Erişim2019Scopus SJRQ3/r/bayburt/13197
  Production of enantiomerically pure (S)-phenyl(pyridin-2-yl)methanol with Lactobacillus paracasei BD101

  Şahin, Engin; Serencam, Hüseyin; Dertli, Enes

  Asymmetric reduction studies of heteroaryl ketones, including phenyl(pyridin-2-yl)methanone in enantioselective form with biocatalysts are very few, and chiral heteroaryl alcohols have been synthesized generally in the small scale. In this study, seven bacterial strains have been used to produce the (S)-phenyl(pyridin-2-yl)methanol in high enantiomeric excess and yield. Among the tested strains, Lactobacillus paracasei BD101, was found to be the best biocatalyst for the reducing phenyl(pyridin-2-yl)methanone to the (S)-phenyl(pyridin-2-yl)methanol at gram scale. The asymmetric bioreduction conditions were systematically optimized using L. paracasei BD101, which demonstrated excellent enantioselectivity and high level of conversion for the bioreduction reaction. (S)-phenyl(pyridin-2-yl)methanol, which is an analgesic, was produced enantiomerically pure form in the first time on gram scale using a biocatalyst. In total, 5.857 g of (S)-phenyl(pyridin-2-yl)methanol in enantiomerically pure form (>99% enantiomeric excess) was obtained in 52 h with 93% yield using whole cells of L. paracasei BD101. Enantiomerically pure (S)-phenyl (pyridin-2-yl)methanol, which is an analgesic, was first produced in the gram scale using a biocatalyst with excellent ee (>99%) and yield (93%).

  AtıfScopus9·WoS7·OpenAlex9

  İncele
• MakaleYalnız künye2019Scopus SJRQ3/r/bayburt/12177
  Production 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.

  AtıfScopus12·WoS10·OpenAlex11

  İncele
• MakaleAçık Erişim2017Scopus SJRQ3/r/bayburt/12263
  Debaryomyces hansenii as a new biocatalyst in the asymmetric reduction of substituted acetophenones

  Şahin, Engin

  Chiral secondary alcohols are convenient mediator for the synthesis of biologically active compounds and natural products. In this study fifteen yeast strains belonging to three food originated yeast species Debaryomyces hansenii, Saccharomyces cerevisiae and Hanseniaspora guilliermondii were tested for their capability for the asymmetric reduction of acetophenone to 1-phenylethanol as biocatalyst microorganisms. Of these strains, Debaryomyces hansenii P1 strain showed an effective asymmetric reduction ability. Under optimized conditions, substituted acetophenones were converted to the corresponding optically active secondary alcohols in up to 99% enantiomeric excess and at high conversion rates. This is the first report on the enantioselective reduction of acetophenone by D. hansenii P1 from pastırma, a fermented Turkish meat product. The preparative scale asymmetric bio reduction of 3-methoxy acetophenone 1g by D. hansenii P1 gave (R)-1-(3-methoxyphenyl) ethanol 2g 82% yield, and >99% enantiomeric excess. Compound 2g can be used for the synthesis of (+)-NPS-R-568 [3-(2-chlorophenyl)-N-[(1R)-1-(3-methoxyphenly) ethyl] propan-1-amine] which have a great potential for the treatment of primary and secondary hyper-parathyroidism. In addition, D. hansenii P1 successfully reduced acetophenone derivatives. This study showed that this yeast can be used industrially to produce enantiomerically pure chiral secondary alcohols, which can be easily converted to different functional groups.

  AtıfScopus25·WoS24·OpenAlex26

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