His-tagged Horse Liver Alcohol Dehydrogenase: Immobilization and application in the bio-based enantioselective synthesis of (S)-arylpropanols

De Wildeman, 2007, Biocatalytic reductions: from lab curiosity to first choice, Acc Chem Res, 40, 1260, 10.1021/ar7001073

Faber, 2011

Hall, 2011, Redox reactions catalyzed by isolated enzymes, Chem Rev, 111, 4088, 10.1021/cr200013n

Hollmann, 2011, Enzyme-mediated oxidations for the chemist, Green Chem, 13, 226, 10.1039/C0GC00595A

Monti, 2011, Redox reactions catalyzed by isolated enzymes, Chem Rev, 111, 4111, 10.1021/cr100334x

Straathof, 2002, The production of fine chemicals by biotransformations, Curr Opin Biotech, 13, 548, 10.1016/S0958-1669(02)00360-9

Liu, 2007, Biotechnol Adv, 25, 369, 10.1016/j.biotechadv.2007.03.002

Cao, 2005, Immobilised enzymes: science or art, Curr Opin Chem Biol, 9, 217, 10.1016/j.cbpa.2005.02.014

Garcia-Galan, 2011, Potential of different enzyme immobilization strategies to improve enzyme performance, Adv Synth Catal, 353, 2885, 10.1002/adsc.201100534

Mateo, 2007, Immobilization of enzymes on heterofunctional epoxy supports, Nat Protoc, 5, 1022, 10.1038/nprot.2007.133

Bes, 1995, Selective oxidation: stabilisation by multipoint attachment of ferredoxin NADP+ reductase, an interesting cofactor recycling enzyme, J Mol Catal A: Chem, 98, 161, 10.1016/1381-1169(95)00019-4

Rocha-Martin, 2009, Purification, immobilization and stabilization of a highly enantioselective alcohol dehydrogenase from Thermus thermophilus HB27 cloned in E. coli, Process Biochem, 44, 1004, 10.1016/j.procbio.2009.04.026

Bolivar, 2012, Stabilization of a highly active but unstable alcohol dehydrogenase from yeast using immobilization and post-immobilization techniques, Process Biochem, 47, 679, 10.1016/j.procbio.2012.01.012

Hanefeld, 2009, Understanding enzyme immobilisation, Chem Soc Rev, 38, 453, 10.1039/B711564B

Guisan, 2006

Mateo, 2001, One-step purification, covalent immobilization, and additional stabilization of poly-His-tagged proteins using novel heterofunctional chelate-epoxy supports, Biotechnol Bioeng, 76, 269, 10.1002/bit.10019

Pessela, 2003, One-step purification, covalent immobilization, and additional stabilization of a thermophilic poly-his-tagged β-galactosidase from Thermus sp. strain t2 by using novel heterofunctional chelate-epoxy sepabeads, Biomacromolecules, 4, 107, 10.1021/bm020086j

Bolivar, 2006, Improvement of the stability of alcohol dehydrogenase by covalent immobilization on glyoxyl-agarose, J Biotechnol, 125, 85, 10.1016/j.jbiotec.2006.01.028

Rocha-Martín, 2012, Characterization and further stabilization of a new anti-prelog specific alcohol dehydrogenase from Thermus thermophilus HB27 for asymmetric reduction of carbonyl compounds, Bioresour Technol, 103, 343, 10.1016/j.biortech.2011.10.018

Grunwald, 1986, Asymmetric oxidoreductions catalyzed by alcohol dehydrogenase in organic solvents, J Am Chem Soc, 108, 6732, 10.1021/ja00281a044

Kelemen-Horvath, 2002, Stereoselective reduction of 2-phenylpropionaldehyde by alcohol dehydrogenase with cofactor regeneration, Chem Pap, 56, 52

Schubert, 2002, Highly enantioselective preparation of multifunctionalized propargylic building blocks, Angew Chem Int Ed, 41, 634, 10.1002/1521-3773(20020215)41:4<634::AID-ANIE634>3.0.CO;2-U

Dworschack, 1977, Kinetics of native and activated isozymes of horse liver alcohol dehydrogenase, Biochemistry, 16, 111, 10.1021/bi00620a018

Cainelli, 1997, Penicillin G acylase mediated synthesis of the enantiopure (S)-3-amino-azetidin-2-one, Tetrahedron: Asymmetry, 8, 3231, 10.1016/S0957-4166(97)00405-9

Cainelli, 2000, Temperature and solvent effects on enzyme stereoselectivity: inversion temperature in kinetic resolutions with lipases, Chem Commun, 2351, 10.1039/b006086k

Cainelli, 2003, Chemo- and enzyme-catalyzed reactions revealing a common temperature-dependent dynamic solvent effect on enantioselectivity, Helv Chim Acta, 86, 3548, 10.1002/hlca.200390299

Cainelli, 2005, Engineered phenylalanine dehydrogenase in organic solvents: homogeneous and biphasic enzymatic reactions, Org Biomol Chem, 3, 4316, 10.1039/b510816k

Cainelli, 2009, Solvent effects on stereoselectivity: more than just an environment, Chem Soc Rev, 38, 990, 10.1039/b802815j

Giacomini, 2007, Highly efficient asymmetric reduction of arylpropionic aldehydes by Horse Liver Alcohol Dehydrogenase through dynamic kinetic resolution, Chem Commun, 4038, 10.1039/b712290j

Giacomini D, Cainelli G, Galletti P, Gucciardo G, Quintavalla A. Enzymatic process for the preparation of chiral 2-arylpropylic alcohols. PCT Int Appl, University of Bologna 2008; WO 2008074717 A2 20080626 CAN 149:104492 AN 2008:774623.

Galletti, 2010, Chemoenzymatic synthesis of (2S)-2-arylpropanols through a dynamic kinetic resolution of 2-arylpropanals with alcohol dehydrogenases, Org Biomol Chem, 8, 4117, 10.1039/c005098a

Pellissier, 2011, Recent developments in dynamic kinetic resolution, Tetrahedron, 67, 3769, 10.1016/j.tet.2011.04.001

Galletti, 2010, One-step oxidation of 2-arylpropanols to 2-arylpropionic acids: improving sustainability in the synthesis of profens, Synlett, 17, 2644

Pollak, 1980, Enzyme immobilization by condensation copolymerization into crosslinked polyacrylamide gels, J Am Chem Soc, 102, 6324, 10.1021/ja00540a026

Parida, 1992, Supported aqueous-phase enzyme catalysis in organic media, Appl Biochem Biotechnol, 33, 1, 10.1007/BF02922179

Ngamsom, 2010, The development and evaluation of a conducting matrix for the electrochemical regeneration of the immobilised co-factor NAD(H) under continuous flow, Org Biomol Chem, 8, 2419, 10.1039/b924100k

Petkova, 2012, Synthesis of silica particles and their application as supports for alcohol dehydrogenases and cofactor immobilizations: conformational changes that lead to switch in enzyme stereoselectivity, Biochim Biophys Acta, 1824, 792, 10.1016/j.bbapap.2012.03.010

Quaglia, 2012, Horse liver alcohol dehydrogenase: new perspectives for an old enzyme, Mol Biotechnol, 52, 244, 10.1007/s12033-012-9542-7

Bradford, 1976, A rapid and sensitive method for the quantitation of microgram quantities of protein utilizing the principle of protein–dye binding, Anal Biochem, 72, 248, 10.1016/0003-2697(76)90527-3

Tischer, 1999, Immobilized enzymes: methods and applications, vol. 200, 95

Carrea, 2000, Properties synthetic applications of enzymes in organic solvents, Angew Chem Int Ed, 39, 2226, 10.1002/1521-3773(20000703)39:13<2226::AID-ANIE2226>3.0.CO;2-L

Klibanov, 2001, Improving enzymes by using them in organic solvents, Nature, 409, 241, 10.1038/35051719

Dickinson, 1967, Substrate specificity and stereospecificity of alcohol dehydrogenases, Nature, 214, 31, 10.1038/214031a0

Jones, 1982, Enzymes in organic synthesis. 23. Effects of organic solvents on horse liver alcohol dehydrogenase-catalyzed oxidation, Can J Chem, 60, 1030, 10.1139/v82-152

Sund, 1963, vol. 7

Wratten, 1965, Kinetic studies with liver alcohol dehydrogenase, Biochemistry, 4, 2442, 10.1021/bi00887a025

Musa, 2011, Recent advances in alcohol dehydrogenase-catalyzed asymmetric production of hydrophobic alcohols, Catal Sci Technol, 1, 1311, 10.1039/c1cy00160d

Kourist, 2011, Biocatalytic strategies for the asymmetric synthesis of profens, recent trends and developments, Green Chem, 13, 2607, 10.1039/c1gc15162b

Sayari, 2007, The N-terminal His-tag affects the enantioselectivity of staphylococcal lipases: a monolayer study, J Colloid Interface Sci, 313, 261, 10.1016/j.jcis.2007.04.053