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  • Öğe
    Recent Advances in the Analysis of Macromolecular Interactions Using the Matrix-Free Method of Sedimentation in the Analytical Ultracentrifuge
    (MDPI, 2015) Harding, S.E., Gillis, R.B., Almutairi, F., Erten, T., Kök, M.Ş., Adams, G.G.,
    Sedimentation in the analytical ultracentrifuge is a matrix free solution technique with no immobilisation, columns, or membranes required and can be used to study self-association and complex or “hetero”-interactions, stoichiometry, reversibility and interaction strength of a wide variety of macromolecular types and across a very large dynamic range (dissociation constants from 10−12 M to 10−1 M). We extend an earlier review specifically highlighting advances in sedimentation velocity and sedimentation equilibrium in the analytical ultracentrifuge applied to protein interactions and mucoadhesion and to review recent applications in protein self-association (tetanus toxoid, agrin), protein-like carbohydrate association (aminocelluloses), carbohydrate-protein interactions (polysaccharide-gliadin), nucleic-acid protein (G-duplexes), nucleic acid-carbohydrate (DNA-chitosan) and finally carbohydrate-carbohydrate (xanthan-chitosan and a ternary polysaccharide complex) interactions
  • Öğe
    Hydrodynamic characterisation of chitosan and its interaction with two polyanions: DNA and xanthan
    (Elsevier, 2015) Almutairi, F., Erten, T., Adams G.G., Hayes, M., McLoughlin P., Kök, M.Ş., Mackie, A.R.,Rowe, A., Harding, S.E.
    Chitosan, a soluble polycationic derivative of insoluble chitin, has been widely considered for use in the food, cosmetic and pharmaceutical industries. Commercial (“C”) and in-house laboratory (“L”) prepared chitosan samples extracted from crustaceous shells with different molecular weight and degrees of acetylation (25% and 15%) were compared with regards to (i) weight–average molecular weight (Mw); (ii) sedimentation coefficient (so20,w) distribution, and (iii) intrinsic viscosity ([η]). These parameters were estimated using a combination of analytical ultracentrifugation (AUC), size exclusion chromatography coupled to multi-angle laser light scattering (SEC–MALS) and differential pressure viscometry. Polydisperse distributions were seen from sedimentation coefficient distributions and elution profiles from SEC–MALS. Mw values obtained for each sample by sedimentation equilibrium measurements were in excellent agreement with those obtained from SEC–MALS. Mark–Houwink–Kuhn–Sakurada (MHKS) and Wales van Holde analyses of the data all suggest a semi-flexible conformation. The principle of co-sedimentation was then used to monitor the interactions of the two different molecular weights of L chitosans with two polyanions, DNA and xanthan (another double helical high molecular weight molecule). Interactions were clearly observed and then quantified from the changes in the sedimentation coefficient distribution of the mixture compared to unmixed controls using sedimentation velocity. The interactions appeared to show a strong dependence on molecular weight. The relevance of this for DNA condensation applications is indicated.
  • Öğe
    Comparative heterogeneity, molecular weights and viscosities of xanthans of different pyruvate and acetate content
    (Elsevier, 2014) Erten, T., Adams, G.G., Foster, T.J., Harding, S.E.
    Introduction: The bacterial exopolysaccharide xanthan is a well-known hydrocolloid, with a high viscosity deriving from its large molecular weight and volume. Materials and methods: Four different xanthans deriving from Xanthomanas campestris e two with similar pyruvate and acetate contents and two with different contents e were characterized in dilute aqueous buffered solution (pH 7.0, ionic strength 0.3 M) using sedimentation velocity and sedimentation equilibrium in the analytical ultracentrifuge, supplemented by dynamic light scattering. Results: This facilitated a comparison with regards heterogeneity (sedimentation coefficient distribution) and molecular weight, despite their large size and low critical overlap concentration. The xanthans were also compared with regard to reduced specific and intrinsic viscosity behaviour. The xanthans generally show strong similarity in properties with the exception of the lowest pyruvate xanthan, a finding which should be useful for future applications of these materials.
  • Öğe
    Ultracentrifuge Methods for the Analysis of Polysaccharides, Glycoconjugates, and Lignins
    (Elsevier, 2015) Harding, S.E., Adams, G.G., Almutairi, F., Alzahrani, Q., Erten, T., Kök, M.Ş., Gillis, R.
    Although like proteins, polysaccharides are synthesized by enzymes, unlike proteins there is no template. This means that they are polydisperse, do not generally have compact folded structures, and are often very large with greater nonideality behavior in solution. This chapter considers the relevant analytical ultracentrifuge methodology available for characterizing these and related carbohydrate-based systems and information this methodology supplies, in terms of sizes, shapes, and interactions using a comprehensive range of examples, including glycoconjugates and lignins. The relevance and potential of recent software developments such as SEDFIT-MSTAR, the Extended Fujita algorithm, and HYDFIT are considered.
  • Öğe
    Avocado–Soybean Unsaponifiables: A Panoply of Potentialities to Be Exploited
    (2020) Salehi, Bahare; Rescigno, Antonio; Dettori, Tunuccia; Calina, Daniela; Docea, Anca Oana; Singh, Laxman; Cebeci, Fatma; Özçelik, Beraat; Bhia, Mohammed; Beirami, Amirreza Dowlati; Sharifi-Rad, Javad; Sharopov, Farukh; Cho, William C.; Martins, Natália
    Avocado and soybean unsaponifiables (ASU) constitute vegetable extracts made from fruits and seeds of avocado and soybean oil. Characterized by its potent anti-inflammatory effects, this ASU mixture is recommended to act as an adjuvant treatment for osteoarthritic pain and slow-acting symptomatic treatment of hip and knee osteoarthritis; autoimmune diseases; diffuse scleroderma and scleroderma-like states (e.g., morphea, sclerodactyly, scleroderma in bands). Besides, it was reported that it can improve the mood and quality of life of postmenopausal women in reducing menopause-related symptoms. This article aims to summarize the studies on biological effects of the avocado–soybean unsaponifiable, its chemical composition, pharmacotherapy as well as applications in autoimmune, osteoarticular and menopausal disorders. Finally, we will also discuss on its safety, toxicological and regulatory practices.
  • Öğe
    Discovery of a bacterial glycoside hydrolase family 3 (GH3) #-glucosidase with myrosinase activity from a Citrobacter strain isolated from soil
    (2016) Albaser, Abdulhadi; Kazana, Eleanna; Bennett, Mark; Cebeci, Fatma; Luang-In, Vijitra; Spanu, Pietro D.; Rossiter, John T.
    A Citrobacter strain (WYE1) was isolated from a UK soil by enrichment using the glucosinolate sinigrin as sole carbon source. The enzyme myrosinase was purified using a combination of ion exchange and gel filtration to give a pure protein of approximately 66 kDa. The N-terminal amino acid and internal peptide sequence of the purified protein were determined and used to identify the gene, which, based on InterPro sequence analysis, belongs to the family GH3, contains a signal peptide, and is a periplasmic protein with a predicted molecular mass of 71.8 kDa. A preliminary characterization was carried out using protein extracts from cell-free preparations. The apparent KM and Vmax were 0.46 mM and 4.91 mmol dm(-3) min(-1) mg(-1), respectively, with sinigrin as substrate. The optimum temperature and pH for enzyme activity were 25 °C and 6.0, respectively. The enzyme was marginally activated with ascorbate by a factor of 1.67.
  • Öğe
    Identification of Proteins Possibly Involved in Glucosinolate Metabolism in L. agilis R16 and E. coli VL8
    (2015) Luang-In, Vijitra; Narbad, Arjan; Cebeci, Fatma; Bennett, Mark; Rossiter, John T.
    This study was aimed to identify sinigrin-induced bacterial proteins potentially involved in the metabolism of glucosinolate in two glucosinolate-metabolising bacteria Lactobacillus agilis R16 and Escherichia coli VL8. Sinigrin (2 mM) was used to induce the proteins in both bacteria under anaerobic incubation for 8 h at 30 C for L. agilis R16 and 37 C for E. coli VL8 and the controls without sinigrin were performed. Allyl isothiocyanate and allyl nitrile as two degradation products of sinigrin were detected in sinigrin-induced cultures of L. agilis R16 (27 % total products) and E. coli VL8 (38 % total products) from a complete sinigrin degradation in 8 h for both bacteria. 2D gel electrophoresis was conducted to identify induced proteins with at least twofold increased abundance. Sinigrin-induced L. agilis R16 and the control produced 1561 and 1543 protein spots, respectively. For E. coli VL8, 1363 spots were detected in sinigrin-induced and 1354 spots in the control. A combination of distinct proteins and upregulated proteins of 32 and 35 spots in L. agilis R16 and E. coli VL8, respectively were detected upon sinigrin induction. Of these, 12 and 16 spots from each bacterium respectively were identified by LC–MS/MS. In both bacteria most of the identified proteins are involved in carbohydrate metabolism, oxidoreduction system and sugar transport while the minority belong to purine metabolism, hydrolysis, and proteolysis. This indicated that sinigrin induction led to the expressions of proteins with similar functions in both bacteria and these proteins may play a role in bacterial glucosinolate metabolism.
  • Öğe
    The matrix effect of blueberry, oat meal and milk on polyphenols, antioxidant activity and potential bioavailability
    (2013) Cebeci, Fatma; Şahin Yeşilçubuk, Neşe
    In recent years, ready-to eat breakfast cereals prepared with fruit ingredients have gained particular attention due to their polyphenolic contents and health promoting effects. In this study, the matrix effect of blueberry, oat meal, whole milk or skimmed milk on polyphenols, antioxidative potential as well as their potential bioavailability were investigated. The phenolic properties of whole milk, skimmed milk, blueberry and oat meal were investigated and the changes in combinations of the ingredients were determined. Milk addition decreased the total phenolic, flavonoid and anthocyanin content of samples statistically and had negative effect on antioxidant activity showing differences among different methods. According to HPLC results, it was not possible to detect catechin in mixtures due to milk addition. In vitro digestion method was used to determine potential bioavailability of phenolic compounds. According to in vitro digestion procedure results, whole or skimmed milk did not affect the total phenolic content of the proportion passing to the blood from intestine.
  • Öğe
    Production of enantiomerically pure (S)-phenyl(pyridin-2-yl)methanol with Lactobacillus paracasei BD101
    (Biocatalysis and Biotransformation, 2019) 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%).
  • Öğe
    First green synthesis of (R)-2-methyl-1-phenylpropan-1-ol using whole-cell Lactobacillus paracasei BD101 biotransformation
    (Biocatalysis and Biotransformation, 2020) 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.
  • Öğe
    Synthesis and Biological Evaluation of Novel Tricyclic Pyrrolidinyl (R)?Alcohols and Amines
    (The Journal of Heterocyclic Chemistry, 2019) Şahin, Engin; Kılıç, Hamdullah; Törnük. Fatih; Dertli, Enes
    Three new tricyclic pyrrolidinyl alcohols and three tricyclic pyrrolidinyl amines were synthesized, and the antibacterial activities of these compounds were tested against Salmonella enterica subsp. enterica serovar Typhimurium, Escherichia coli O157:H7, Staphylococcus aureus, and Listeria monocytogenes. All tested pyrrolidinyl alcohols and amines showed antibacterial activity to the tested pathogens, but this activity was dependent on the final concentration of the tested compound, and the structure of these compounds were also important for this antibacterial activity. Of the tested compounds, (2R)‐2‐(octahydro‐4,8‐ethanocyclohepta[c]pyrrol‐2(1H)‐yl)‐2‐phenylethanamine (2c) was the most effective compound among the tested pyrrolidinyl alcohols and amines. This study shows a good example of finding new antimicrobials in order to control pathogenic bacteria.
  • Öğe
    Production of enantiopure chiral aryl heteroaryl carbinols using whole?cell Lactobacillus paracasei biotransformation
    (Synthetic Communications, 2020) 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.
  • Öğe
    Candida zeylanoides as whole-cell biocatalyst to perform asymmetric bioreduction of benzophenone derivatives
    (Synthetic Communications, 2020) Şahin, Engin
    Candida zeylanoides P1 was investigated as whole cell biocatalyst for the bioreduction of biaryl prochiral ketones into chiral carbinols, which can be used as pharmaceutical intermediate. Bioreduction of different biaryl ketones was carried out to their corresponding chiral biaryl carbinols such as (S)-(4-chlorophenyl) (phenyl) methanol (2a), which can be used in the synthesis of L-cloperastine drug, with antitussive, antiepidemic activity and bronchial musculature relaxant characteristics, in gram scale, enantiopure form (>99%) and excellent yields. The selectivity of C. zeylanoides P1 in enantioselective reduction of biaryl ketones was not affected by the steric and electronic effects of substrates. The current method demonstrates an encouraging green chemistry approach for the production of biaryl secondary chiral alcohols of pharmaceutical importance in mild, inexpensive and environmentally friendly process. The present study has many benefits since this yeast biocatalyst were successfully applied bioreduction of structurally bulky prochiral substrates, which cannot be reducted by chemical catalysis.
  • Öğe
    Biocatalyzed Enantiomerically Pure Production of (S)?Phenyl(thiophen?2?yl)methanol
    (The Journal of Heterocyclic Chemistry, 2019) Şahin, Engin; Dertli, Enes
    Chiral aryl heteroaryl methanols are important precursors for the synthesis of pharmaceutically important molecules. The aims of this study were to use a biocatalyst that could efficiently bioreduce phenyl(thiophen‐2‐yl)methanone 1 to (S)‐phenyl(thiophen‐2‐yl)methanol 2, to identify the impact of the physicochemical factors that might affect the bioreduction by the biocatalyst, and to obtain multigram production of aryl heteroaryl secondary alcohol 2 with the biocatalyst under optimized conditions. Over the years, the (S)‐phenyl(thiophen‐2‐yl)methanol was synthesized on a small scale using a chemical catalyst without its enantiomerically pure form. In this study, Lactobacillus paracasei BD101 was used for the asymmetric reduction of phenyl(thiophen‐2‐yl)methanone to (S)‐phenyl(thiophen‐2‐yl)methanol in the large‐scale production. The asymmetric bioreduction conditions were systematically optimized, and the production of 3.77 g of (S)‐phenyl(thiophen‐2‐yl)methanol was carried out in enantiomerically pure form >99% enantiomeric excess (ee), >99% conversion, and 90% yield. This method obtained with this biocatalyst is a process that can be used industrially in terms of conversion, ee, and yield. This study provides guidance for the application of L. paracasei BD101 in the production of optically active aryl heteroaryl alcohols.
  • Öğe
    Debaryomyces hansenii as a new biocatalyst in the asymmetric reduction of substituted acetophenones
    (Biocatalysis and Biotransformation, 2017) 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.
  • Öğe
    Green synthesis of chiral aromatic alcohols with Lactobacillus kefiri P2 as a novel biocatalyst
    (Synthetic Communications, 2020) 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.
  • Öğe
    Production of enantiomerically enriched chiral carbinols using Weissella paramesenteroides as a novel whole cell biocatalyst
    (Biocatalysis and Biotransformation, 2019) 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. Weissella paramesenteroides as a food originated yeast species is capable of bioreduction of prochiral ketones to secondary chiral alcohols in one enantiomeric form.
  • Öğe
    Whole cell application of Lactobacillus paracasei BD101 to produce enantiomerically pure (S)?cyclohexyl(phenyl)methanol
    (Chirality, 2019) 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.
  • Öğe
    Synthesis of Enantiomerically Enriched Drug Precursors by Lactobacillus paracasei BD87E6 as a Biocatalyst
    (Chemistry Biodiversity, 2018) Öksüz, Selda; Şahin, Engin; Dertli, Enes
    Global sales of single enantiomeric drug products are growing at an alarming rate every year. A total of 7 bacterial strains were screened for their ability to reduce acetophenones to its corresponding alcohol. Among these strains Lactobacillus paracasei BD87E6 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 Lactobacillus paracasei BD87E6, which showed high enantioselectivity and conversion for the bioreduction. The preparative scale asymmetric reduction of 3‐methoxyacetophenone (1h) by Lactobacillus paracasei BD87E6 gave (R)‐1‐(3‐methoxyphenyl)ethanol (2h) with 92% yield and 99% enantiomeric excess. Compound 2h could be used for the synthesis of (S)‐rivastigmine which has a great potential for the treatment of Alzheimer's disease. This study demonstrates that Lactobacillus paracasei BD87E6 can be used as a biocatalyst to obtain chiral carbinol with excellent yield and selectivity. The whole cell catalyzed the reductions of ketone substrates on the preparative scale, demonstrating that Lactobacillus paracasei BD87E6 would be a valuable biocatalyst for the preparation of chiral aromatic alcohols of pharmaceutical interest.
  • Öğe
    Highly Enantioselective Production of Chiral Secondary Alcohols with Candida zeylanoides as a New Whole Cell Biocatalyst
    (Chemistry Biodiversity, 2017) 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.