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Research Articles

Biocatalytic asymmetric synthesis of (S)-1-indanol using Lactobacillus paracasei BD71

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Pages 386-392 | Received 10 Nov 2020, Accepted 04 Nov 2021, Published online: 16 Nov 2021

References

  • Alcolea-Palafox M, Posada-Moreno P, Ortuño-Soriano I, Pacheco-del-Cerro JL, Martínez-Rincón C, Rodríguez-Martínez D, Pacheco-Cuevas L. 2014. Research strategies developed for the treatment of Alzheimer’s disease. Reversible and pseudo-irreversible inhibitors of acetylcholinesterase: structure–activity relationships and drug design. Front Drug Des Discov. 6:426–477.
  • Bai D, He J, Ouyang B, Huang J, Wang P. 2017. Biocatalytic asymmetric synthesis of chiral aryl alcohols. Prog Chem. 29(5):49–501.
  • Baydaş Y, Dertli E, Şahin E. 2020. Green synthesis of chiral aromatic alcohols with Lactobacillus kefiri P2 as a novel biocatalyst. Synth Commun. 50(7):1035–1045.
  • Bennamane M, Razi S, Zeror S, Aribi-Zouioueche L. 2018. Preparation of chiral phenylethanols using various vegetables grown in Algeria. Biocatal Agric Biotechnol. 14:52–56.
  • Biswas D, Pandya V, Singh AK, Mondal AK, Kumaran S. 2012. Co-factor binding confers substrate specificity to xylose reductase from Debaryomyces hansenii. PLOS One. 7(9):e45525.
  • Borazjani M, Mehdinia A, Ziaei E, Jabbari A, Maddah M. 2017. Enantioselective electrochemical sensor for R-mandelic acid based on a glassy carbon electrode modified with multi-layers of biotin-loaded overoxidized polypyrrole and nanosheets of reduced graphene oxide. Microchim Acta. 184(2):611–620.
  • Caron D, Coughlan AP, Simard M, Bernier J, Piché Y, Chênevert R. 2005. Stereoselective reduction of ketones by Daucus carota hairy root cultures. Biotechnol Lett. 27(10):713–716.
  • de Sousa Fonseca T, da Silva MR, de Oliveira MDCF, de Lemos TLG, de A, Marques R, de Mattos MC. 2015. Chemoenzymatic synthesis of rasagiline mesylate using lipases. Appl Catal A Gen. 492:76–82.
  • Dertli E, Mercan E, Arıcı M, Yılmaz MT, Sağdıç O. 2016. Characterisation of lactic acid bacteria from Turkish sourdough and determination of their exopolysaccharide (EPS) production characteristics. LWT Food Sci Technol. 71:116–124.
  • Hatti-Kaul R, Chen L, Dishisha T, Enshasy HE. 2018. Lactic acid bacteria: from starter cultures to producers of chemicals. FEMS Microbiol Lett. 365(20):fny213.
  • Mączka W, Wińska K, Grabarczyk M, Galek R. 2019. Plant-mediated enantioselective transformation of indan-1-one and indan-1-ol. Catalysts. 9(10):844.
  • Mastai Y. 2009. Enantioselective crystallization on nanochiral surfaces. Chem Soc Rev. 38(3):772–780.
  • Nagai T, Sakurai S, Natori N, Hataoka M, Kinoshita T, Inoue H, Hanaya K, Shoji M, Sugai T. 2018. Synthesis of enantiomerically enriched drug precursors and an insect pheromone via reduction of ketones using commercially available carbonyl reductase screening kit “Chiralscreen® OH". Bioorg Med Chem. 26(7):1304–1313.
  • Nagaki M, Soma N, Ono K, Yamanouchi K, Tsujiguchi T, Kawakami J, Chounan Y. 2019. Biotransformation of indanol, fluorenol and their analogs using tissue-cultured cells and their antimicrobial activity. Trans Mat Res Soc Japan. 44(1):29–33.
  • Ni Y, Xu JH. 2012. Biocatalytic ketone reduction: a green and efficient access to enantiopure alcohols. Biotechnol Adv. 30(6):1279–1288.
  • Pedrini P, Giovannini PP, Mantovani M, Andreotti E, Colalongo C. 2009. Reduction screening with endophytic fungi: synthesis of homochiral secondary alcohols. J Mol Catal B Enzym. 60(3–4):145–150.
  • Perna FM, Ricci MA, Scilimati A, Mena MC, Pisano I, Palmieri L, Agrimi G, Vitale P. 2016. Cheap and environmentally sustainable stereoselective arylketones reduction by Lactobacillus reuteri whole cells. J Mol Catal B Enzym. 124:29–37.
  • Pu W, Huizhen S, Liming S, Junyao HE, Yaping LÜ. 2011. Asymmetric bioreduction of 3, 5-bis (trifluoromethyl) acetophenone to its corresponding alcohol by Candida tropicalis. Chin J Chem Eng. 19:1028–1032.
  • Ranjan P, Pandey A, Binod P. 2017. Resolution of enantiopure (S)-1-(1-napthyl) ethanol from racemic mixture by a novel Bacillus cereus isolate. J Basic Microbiol. 57(9):762–769.
  • Şahin E, Serencam H, Dertli E. 2019. Whole cell application of Lactobacillus paracasei BD101 to produce enantiomerically pure (S)-cyclohexyl(phenyl)methanol. Chirality. 31(3):211–218.
  • Şahin E. 2019. Green synthesis of enantiopure (S)-1-(benzofuran-2-yl)ethanol by whole-cell biocatalyst. Chirality. 31(10):892–897.
  • Şahin E. 2020. Synthesis of enantiopure (S)-6-chlorochroman-4-ol using whole-cell Lactobacillus paracasei biotransformation. Chirality. 32(3):400–406.
  • Şahin E, Dertli E. 2017. Highly enantioselective production of chiral secondary alcohols with Candida zeylanoides as a new whole cell biocatalyst. Chem Biodivers. 14(9):e1700121.
  • Salvi NA, Chattopadhyay S. 2016. Laboratory scale-up synthesis of chiral carbinols using Rhizopus arrhizus. Tetrahedron Asymmetry. 27(4–5):188–192.
  • Secundo F, Phillips RS. 1996. Effects of pH on enantiospecificity of alcohol dehydrogenases from Thermoanaerobacter ethanolicus and horse liver. Enzyme Microb Technol. 19(7):487–492.
  • Singh A, Chisti Y, Banerjee UC. 2012. Stereoselective biocatalytic hydride transfer to substituted acetophenones by the yeast Metschnikowia koreensis. Process Biochem. 47(12):2398–2404.
  • Solano DM, Hoyos P, Hernáiz MJ, Alcántara AR, Sánchez-Montero JM. 2012. Industrial biotransformations in the synthesis of building blocks leading to enantiopure drugs. Bioresour Technol. 115:196–207.
  • Soni R, Jolley KE, Gosiewska S, Clarkson GJ, Fang Z, Hall TH, Treloar BN, Knighton RC, Wills M. 2018. Synthesis of enantiomerically pure and racemic benzyl-tethered Ru (II)/TsDPEN complexes by direct arene substitution: further complexes and applications. Organometallics. 37(1):48–64.
  • Stompor M, Kałużny M, Żarowska B. 2016. Biotechnological methods for chalcone reduction using whole cells of Lactobacillus, Rhodococcus and Rhodotorula strains as a way to produce new derivatives. Appl Microbiol Biotechnol. 100(19):8371–8384.
  • Xie Y, Xu JH, Lu WY, Lin GQ. 2009. Adzuki bean: a new resource of biocatalyst for asymmetric reduction of aromatic ketones with high stereoselectivity and substrate tolerance. Bioresour Technol. 100(9):2463–2468.
  • Yadav GD, Devendran S. 2012. Lipase catalyzed kinetic resolution of (±)-1-(1-naphthyl) ethanol under microwave irradiation. J Mol Catal B Enzym. 81:58–65.
  • Yadav JS, Nanda S, Reddy PT, Rao AB. 2002. Efficient enantioselective reduction of ketones with Daucus carota root. J Org Chem. 67(11):3900–3903.
  • Yadav JS, Reddy BVS, Sreelakshmi C, Rao AB. 2009. Enantioselective reduction of prochiral ketones employing sprouted Pisum sativa as biocatalyst. Synthesis. 2009(11):1881–1885.
  • Yılmaz D, Şahin E, Dertli E. 2017. Highly enantioselective production of chiral secondary alcohols using Lactobacillus paracasei BD 101 as a new whole cell biocatalyst and evaluation of their antimicrobial effects. Chem Biodivers. 14(11):e1700269.
  • Yin C, Dong XQ, Zhang X. 2018. Iridium/f‐amphol‐catalyzed efficient asymmetric hydrogenation of benzo‐fused cyclic ketones. Adv Synth Catal. 360(22):4319–4324.
  • Yu S, Li H, Lu Y, Zheng G. 2018. A catalyst from Burkholderia cenocepacia for efficient anti-Prelog’s bioreduction of 3, 5-bis (trifluoromethyl) acetophenone. Appl Biochem Biotechnol. 184(4):1319–1331.
  • Zhang L, Tang Y, Han Z, Ding K. 2019. Lutidine-based chiral pincer manganese catalysts for enantioselective hydrogenation of ketones. Angew Chem Int Ed Engl. 58(15):4973–4977.
  • Zilbeyaz K, Kurbanoglu EB, Kilic H. 2016. Preparation of enantiomerically pure (S)‐(−)‐1‐(1′‐naphthyl)‐ethanol by the Fungus Alternaria alternata. Chirality. 28(10):669–673.

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