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Research Articles

Production of enantiomerically enriched chiral carbinols using whole-cell biocatalyst

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Pages 29-37 | Received 22 Jun 2020, Accepted 12 Oct 2020, Published online: 21 Oct 2020

References

  • Alsafadi D, Alsalman S, Paradisi F. 2017. Extreme halophilic alcohol dehydrogenase mediated highly efficient syntheses of enantiopure aromatic alcohols. Org Biomol Chem. 15(43):9169–9175.
  • Amidjojo M, Weuster-Botz D. 2005. Asymmetric synthesis of the chiral synthon ethyl (S)-4-chloro-3-hydroxybutanoate using Lactobacillus Kefiri. Tetrahedron Asymmetry. 16(4):899–901.
  • 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.
  • Bigler R, Huber R, Mezzetti A. 2015. Highly enantioselective transfer hydrogenation of ketones with chiral (NH)2 P2 macrocyclic iron(II) complexes. Angew Chem Int Ed Engl. 54(17):5171–5174.
  • Bosak A, Smilovic IG, Sinko G, Vinkovic V, Kovarik Z. 2012. Metaproterenol, isoproterenol, and their bisdimethylcarbamate derivatives as human cholinesterase inhibitors. J Med Chem. 55(15):6716–6723.
  • Cai S, Shao N, Chen Y, Li A, Pan J, Zhu H, Zou H, Zeng S, Sun L, Zhao J. 2019. Enantioselective reduction of α,β-unsaturated ketones and aryl ketones by perakine reductase. Org Lett. 21(12):4411–4414.
  • Carlos AMM, Contreira ME, Martins BS, Immich MF, Moro AV, Lüdtke DS. 2015. Catalytic asymmetric arylation of aliphatic aldehydes using a B/Zn exchange reaction. Tetrahedron. 71(8):1202–1206.
  • Carlsen PHJ, Katsuki T, Martin VS, Sharpless KB. 1981. A greatly improved procedure for ruthenium tetroxide catalyzed oxidations of organic compounds. J Org Chem. 46(19):3936–3938.
  • Caron D, Coughlan AP, Simard M, Bernier J, Piche Y, Chenevert R. 2005. Stereoselective reduction of ketones by Daucus carota hairy root cultures. Biotechnol Lett. 27(10):713–716.
  • Chartrain M, Mathre D, Reamer RA, Patel S, Shinkai I, Greasham R. 1997. Asymmetric bioreduction of cyclohexylphenyl ketone to its corresponding alcohol (+) cyclohexylphenyl alcohol by the yeast Candida magnoliae MY 1785. J Ferment Bioeng. 83(4):395–396.
  • Chen F, Zhang Y, Yu L, Zhu SJAC. 2017. Enantioselective NiH/Pmrox‐catalyzed 1, 2‐ reduction of α, β‐unsaturated ketones. Angew Chem. 129(8):2054–2057.
  • Cicco L, Ríos-Lombardía N, Rodríguez-Álvarez MJ, Morís F, Perna FM, Capriati V, García-Álvarez J, González-Sabín J. 2018. Programming cascade reactions interfacing biocatalysis with transition-metal catalysis in deep eutectic solvents as biorenewable reaction media. Green Chem. 20(15):3468–3475.
  • Devendran S, Yadav GD. 2014. Lipase-catalyzed kinetic resolution of (±)-1-(2-Furyl) ethanol in nonaqueous media. Chirality. 26(6):286–292.
  • Devendran S, Yadav GD. 2014. Microwave assisted enzymatic kinetic resolution of (±)-1-phenyl-2-propyn-1-Ol in nonaqueous media. Biomed Res Int. 2014:482678–482679.
  • Ema T, Ura N, Yoshii M, Korenaga T, Sakai T. 2009. Empirical method for predicting enantioselectivity in catalytic reactions: demonstration with lipase and oxazaborolidine. Tetrahedron. 65(46):9583–9591. ‐
  • Gandomkar S, Habibi Z, Mohammadi M, Yousefi M, Salimi S. 2015. Enantioselective resolution of racemic ibuprofen esters using different lipases immobilized on epoxy-functionalized silica. Biocatal Agric Biotechnol. 4(4):550–554.
  • Goldberg K, Schroer K, Lütz S, Liese A. 2007. Biocatalytic Ketone reduction-a powerful tool for the production of chiral alcohols-part I: processes with isolated enzymes. Appl Microbiol Biotechnol. 76(2):237–248.
  • Guo J, Chen J, Lu Z. 2015. Cobalt-catalyzed asymmetric hydroboration of aryl ketones with pinacolborane. Chem Commun (Camb). 51(26):5725–5727.
  • Hayes AM, Morris DJ, Clarkson GJ, Wills MA. 2005. A class of ruthenium(II) catalyst for asymmetric transfer hydrogenations of ketones. J Am Chem Soc. 127(20):7318–7319.
  • He P, Zheng H, Liu X, Lian X, Lin L, Feng X. 2014. Asymmetric Reduction of α-amino ketones with a KBH4 solution catalyzed by chiral Lewis acids . Chemistry. 20(42):13482–13486.
  • Hiratake J, Inagaki M, Nishioka T, Oda J. 1988. Irreversible and highly enantioselective acylation of 2-Halo- 1-arylethanols in organic solvents catalyzed by a lipase from pseudomonas fluorescens. J Org Chem. 53(26):6130–6133.
  • Hollmann F, Arends IWCE, Holtmann D. 2011. Enzymatic reductions for the chemist. Green Chem. 13(9):2285–2314.
  • Homann MJ, Vail RB, Previte E, Tamarez M, Morgan B, Dodds DR, Zaks A. 2004. Rapid identification of enantioselective ketone reductions using targeted microbial libraries. Tetrahedron. 60(3):789–797.
  • Jozwiak K, Khalid C, Tanga MJ, Berzetei-Gurske I, Jimenez L, Kozocas JA, Woo A, Zhu W, Xiao R, Abernethy DR, et al. 2007. Comparative molecular field analysis of the binding of the stereoisomers of fenoterol and fenoterol derivatives to the beta2 adrenergic receptor. J Med Chem. 50(12):2903–2915.
  • Kadotani S, Nokami T, Itoh T. 2019. Enhanced activity and modified substrate-favoritism of Burkholderia cepacia lipase by the treatment with a pyridinium alkyl-PEG sulfate ionic liquid. Tetrahedron. 75(4):441–447.
  • Kang BC, Shin SH, Yun J, Ryu DH. 2017. Highly enantioselective hydrosilylation of ketones catalyzed by a chiral oxazaborolidinium ion. Org Lett. 19(23):6316–6319.
  • Kapoor M, Anand N, Ahmad K, Koul S, Chimni SS, Taneja SC, Qazi GN. 2005. Synthesis of β-adrenergic blockers (R)-(-)-nifenalol and (S)-(+)-sotalol via a highly efficient resolution of a bromohydrin precursor. Tetrahedron: Asymmetry. 16(3):717–725.
  • Karthikeyan J, Jeganmohan M, Cheng C-H. 2010. Cobalt-catalyzed addition reaction of organoboronic acids with aldehydes: highly enantioselective synthesis of diarylmethanols . Chemistry. 16(30):8989–8992.
  • Kunkalkar RA, Fernandes RA. 2019. Protecting-group-free total synthesis of chatenaytrienin-2. J Org Chem. 84(18):12216–12220.
  • Liese A, Seelbach K, Wandry C. 2000. Industrial biotransformations. New York: Wiley-VCH; p. 423.
  • Ling F, Nian S, Chen J, Luo W, Wang Z, Lv Y, Zhong W. 2018. Development of ferrocene-based diamine-phosphine-sulfonamide ligands for iridium-catalyzed asymmetric hydrogenation of ketones. J Org Chem. 83(18):10749–10761.
  • 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.
  • Maczka WK, Mironowicz A. 2002. Enantioselective hydrolysis of 1-aryl ethyl acetates and reduction of aryl methyl ketones using carrot, celeriac and horseradish enzyme systems. Tetrahedron Asymmetry. 13:2299–2302.
  • Magnus NA, Anzeveno PB, Coffey DS, Hay DA, Laurila ME, Schkeryantz JM, Shaw BW, Staszak MA. 2007. Optimized catalytic enantioselective aryl transfer process gives access to mGlu2 receptor potentiators. Org Process Res Dev. 11(3):560–567.
  • Mandal D, Ahmad A, Khan MI, Kumar R. 2004. Enantioselective bioreduction of acetophenone and its analogous by the fungus Trichothecium sp. J Mol Catal B Enzym. 27(2–3):61–63.
  • Matsuda T, Yamagishi Y, Koguchi S, Iwai N, Kitazume T. 2006. An effective method to use ionic liquids as reaction media for asymmetric reduction by Geotrichum candidum. Tetrahedron Lett. 47(27):4619–4622.
  • Matsunami A, Ikeda M, Nakamura H, Yoshida M, Kuwata S, Kayaki Y. 2018. Accessible Bifunctional oxy-tethered ruthenium (II) catalysts for asymmetric transfer hydrogenation. Org Lett. 20:213–5218.
  • Muthineni N, Arnipally MS, Bojja S, Meshram HM, Srivastava AK, Adari BR. 2016. Green approach towards the synthesis of chiral alcohols using functionalized alginate immobilized Saccharomyces cerevisiae cells. J Mol Catal B Enzym. 134:233–237.
  • 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.
  • Nishihara TT, Shiomi A, Kadotani S, Nokami T, Itoh T. 2017. Remarkably improved stability and enhanced activity of a Burkholderia cepacia lipase by coating with a triazolium alkyl-PEG sulfate ionic liquid. Green Chem. 19(21):5250–5256.
  • Panke S, Wubbolts M. 2005. Advances in biocatalytic synthesis of pharmaceutical intermediates. Curr Opin Chem Biol. 9(2):188–194.
  • Patel RN. 2013. Biocatalytic synthesis of chiral alcohols and amino acids for development of pharmaceuticals. Biomolecules. 3(4):741–777.
  • Patel RN. 2002. Microbial/enzymatic synthesis of chiral intermediates for pharmaceuticals. Enzyme Microb Technol. 31(6):804–826.
  • Patel RN, Goswami A, Chu L, Donovan MJ, Nanduri V, Goldberg S, Johnston R, Siva PJ, Nielsen B, Fan J, et al. 2004. Enantioselective microbial reduction of substituted acetophenones. Tetrahedron Asymmetry. 15(8):1247–1258.,
  • Rocha LC, Ferreira HV, Pimenta EF, Berlinck RGS, Seleghim MHR, Javaroti DCD, Sette LD, Bonugli RC, Porto ALM. 2009. Bioreduction of alpha-chloroacetophenone by whole cells of marine fungi . Biotechnol Lett. 31(10):1559–1563.
  • Şahin E. 2020a. Production of enantiopure chiral aryl heteroaryl carbinols using whole‐cell Lactobacillus paracasei biotransformation. Synth Commun. 50(4):549–557.
  • Şahin E. 2020b. Synthesis of enantiopure (S)-6-chlorochroman-4-ol using whole-cell Lactobacillus paracasei biotransformation. Chirality. 32(3):400–406.
  • Şahin E. 2020c. Candida zeylanoides as whole-cell biocatalyst to perform asymmetric bioreduction of benzophenone derivatives. Synth Commun. 50(4):612–619.
  • Şahin E. 2020d. First green synthesis of (R)-2-methyl-1-phenylpropan-1-ol using whole-cell Lactobacillus paracasei BD101 biotransformation. Biocatal Biotransform. 38(2):138–143.
  • Şahin E, Dertli E. 2019. Biocatalyzed Enantiomerically Pure Production of (S)‐Phenyl (thiophen‐2‐yl) methanol. J Heterocyclic Chem. 56(10):2884–2888.
  • 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.
  • Salvi NA, Chattopadhyay S. 2016. Laboratory scale-up synthesis of chiral carbinols using Rhizopus arrhizus. Tetrahedron. 27(4-5):188–192.
  • Sato I, Saito T, Soai K. 2000. Solvent-free catalytic enantioselective addition of diethylzinc to aldehydes. Chem Commun. 24(24):2471–2472.
  • Schmidt F, Stemmler RT, Rudolph J, Bolm C. 2006. Catalytic asymmetric approaches towards enantiomerically enriched diarylmethanols and diarylmethylamines. Chem Soc Rev. 35(5):454–470.
  • Slagbrand T, Kivijärvi T, Adolfsson H. 2015. Bimetallic catalysis: asymmetric transfer hydrogenation of sterically hindered ketones catalyzed by ruthenium and potassium. ChemCatChem. 7(21):3445–3449.
  • Sun Z, Lonsdale R, Ilie A, Li G, Zhou J, Reetz MT. 2016. Catalytic asymmetric reduction of difficult-to-reduce ketones: triple-code saturation mutagenesis of an alcohol dehydrogenase. ACS Catal. 6(3):1598–1605.
  • Tan AWI, Fischbach M, Huebner H, Buchholz R, Hummel W, Daussmann T, Wandrey C, Liese A. 2006. Synthesis of Enantiopure (5R)-Hydroxyhexane-2-One with Immobilised Whole Cells of Lactobacillus Kefiri. Appl Microbiol Biotechnol. 71(3):289–293.
  • Touchard F, Bernard M, Fache F, Lemaire M. 1999. Ureas and thioureas as Rh-ligands for the enantioselective hydride transfer reduction of acetophenone. J Mol Catal A Chem. 140(1):1–11.
  • Touge T, Nara H, Fujiwhara M, Kayaki Y, Ikariya T. 2016. Efficient access to chiral benzhydrols via asymmetric transfer hydrogenation of unsymmetrical benzophenones with bifunctional oxo-tethered ruthenium catalysts. J Am Chem Soc. 138(32):10084–10087.
  • Tozlu C, Şahin E, Serencam H, Dertli E. 2019. Production of enantiomerically enriched chiral carbinols using Weissella paramesenteroides as a novel whole cell biocatalyst. Biocatal Biotransform. 37(5):388–398.
  • Truppo MD, Pollard D, Devine P. 2007. Enzyme-catalyzed enantioselective diaryl ketone reductions. Org Lett. 9(2):335–338.
  • Weckbecker A, Hummel W. 2006. Cloning, expression, and characterization of an (R)-specific alcohol dehydrogenase from Lactobacillus Kefiri. Biocatal Biotransform. 24(5):380–389.
  • Wei S, Messerer R, Tsogoeva SB. 2011. Asymmetric synthesis of β-adrenergic blockers through multistep one-pot transformations involving in situ chiral organocatalyst formation. Chemistry. 17(51):14380–14384.
  • White JD, Amedio JC. 1989. Total synthesis of geodiamolide A, a novel cyclodepsipeptide of marine origin. J Org Chem. 54(4):736–738.
  • Wu W, Liu S, Duan M, Tan X, Chen C, Xie Y, Lan Y, Dong X-Q, Zhang X. 2016. Iridium catalysts with f-amphox ligands: asymmetric hydrogenation of simple ketones. Org Lett. 18(12):2938–2941.
  • Wu X, Wang Y, Ju J, Chen C, Liu N, Chen Y. 2009. Enantioselective synthesis of ethyl (S)-2-hydroxy-4-phenylbutyrate by recombinant diketoreductase. Tetrahedron Asymmetry. 20(21):2504–2509.
  • Wujkowska Z, Jarzyński S, Pieczonka AM, Leśniak S, Rachwalski M. 2016. Highly enantioselective addition of arylzinc reagents to aldehydes promoted by chiral aziridine alcohols. Tetrahedron Asymmetry. 27(24):1238–1244.
  • 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 SJ, Reddy BVS, Sreelakshmi C, Rao AB. 2009. Enantioselective reduction of prochiral ketones employing Sprouted Pisum sativa as biocatalyst. Synthesis. 2009(11):1881–1885.
  • Ye Q, Cheng T, Zhao Y, Zhao J, Jin R, Liu G. 2015. One-pot cascade hydration–asymmetric transfer hydrogenation as a practical strategy to construct chiral b-adrenergic receptor blockers. ChemCatChem. 7(12):1801–1805.
  • Yu J, Long J, Yang Y, Wu W, Xue P, Chung LW, Dong X-Q, Zhang X. 2017. Iridium-catalyzed asymmetric hydrogenation of ketones with accessible and modular ferrocene-based amino-phosphine acid (f-Ampha) Ligands. Org Lett. 19(3):690–693.
  • Zhou F, Hu X, Gao M, Tanyu Cheng T, Liu G. 2016. An imidazolium-modified chiral rhodium/diamine functionalized periodic mesoporous organosilica for asymmetric transfer hydrogenation of α-haloketones and benzils in aqueous medium. Green Chem. 18(20):5651–5657.

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