Expanding the organic toolbox: a guide to integrating biocatalysis in synthesis

Improving enzymes by using them in organic solvents

Klibanov, A. M. (2001) · Nature · doi:10.1038/35051719 · Cited by 2,152

Enzyme Immobilization: The Quest for Optimum Performance

Sheldon, R. A. (2007) · Advanced Synthesis & Catalysis · doi:10.1002/adsc.200700082 · Cited by 2,077

Industrial applications of microbial lipases

Hasan, F., Shah, A. A., & Hameed, A. (2006) · Enzyme and Microbial Technology · doi:10.1016/j.enzmictec.2005.10.016 · Cited by 1,951

Biocatalytic Asymmetric Synthesis of Chiral Amines from Ketones Applied to Sitagliptin Manufacture

Savile, C. K., Janey, J. M., Mundorff, E. C., Moore, J. C., Tam, S., Jarvis, W. R., Colbeck, J. C., Krebber, A., Fleitz, F. J., Brands, J., et al. (2010) · Science · doi:10.1126/science.1188934 · Cited by 1,756

Biocatalysis in Ionic Liquids

van Rantwijk, F., & Sheldon, R. A. (2007) · Chemical Reviews · doi:10.1021/cr050946x · Cited by 1,561

Understanding enzyme immobilisation

Hanefeld, U., Gardossi, L., & Magner, E. (2009) · Chem. Soc. Rev. · doi:10.1039/b711564b · Cited by 1,237

Expanding GSK's solvent selection guide – embedding sustainability into solvent selection starting at medicinal chemistry

Henderson, R. K., Jiménez-González, C., Constable, D. J. C., Alston, S. R., Inglis, G. G. A., Fisher, G., Sherwood, J., Binks, S. P., & Curzons, A. D. (2011) · Green Chemistry · doi:10.1039/c0gc00918k · Cited by 1,140

Advances in enzyme immobilisation

Brady, D., & Jordaan, J. (2009) · Biotechnology Letters · doi:10.1007/s10529-009-0076-4 · Cited by 809

Enzymatic Polymer Synthesis: An Opportunity for Green Polymer Chemistry

Kobayashi, S., & Makino, A. (2009) · Chemical Reviews · doi:10.1021/cr900165z · Cited by 609

Multi‐Enzymatic Cascade Reactions: Overview and Perspectives

Ricca, E., Brucher, B., & Schrittwieser, J. H. (2011) · Advanced Synthesis & Catalysis · doi:10.1002/adsc.201100256 · Cited by 529

Hydrolase-catalyzed biotransformations in deep eutectic solvents

Gorke, J. T., Srienc, F., & Kazlauskas, R. J. (2008) · Chemical Communications · doi:10.1039/b716317g · Cited by 529

Guidelines and Cost Analysis for Catalyst Production in Biocatalytic Processes

Tufvesson, P., Lima-Ramos, J., Nordblad, M., & Woodley, J. M. (2011) · Organic Process Research & Development · doi:10.1021/op1002165 · Cited by 496

Cytochrome P450 monooxygenases: an update on perspectives for synthetic application

Urlacher, V. B., & Girhard, M. (2012) · Trends in Biotechnology · doi:10.1016/j.tibtech.2011.06.012 · Cited by 493

Recent advances of enzymatic reactions in ionic liquids

Moniruzzaman, M., Nakashima, K., Kamiya, N., & Goto, M. (2010) · Biochemical Engineering Journal · doi:10.1016/j.bej.2009.10.002 · Cited by 450

Baeyer−Villiger Monooxygenases: More Than Just Green Chemistry

Leisch, H., Morley, K., & Lau, P. C. K. (2011) · Chemical Reviews · doi:10.1021/cr1003437 · Cited by 443

A green-by-design biocatalytic process for atorvastatin intermediate

Ma, S. K., Gruber, J., Davis, C., Newman, L., Gray, D., Wang, A., Grate, J., Huisman, G. W., & Sheldon, R. A. (2010) · Green Chem. · doi:10.1039/b919115c · Cited by 440

Regio- and stereoselectivity of P450-catalysed hydroxylation of steroids controlled by laboratory evolution

Kille, S., Zilly, F. E., Acevedo, J. P., & Reetz, M. T. (2011) · Nature Chemistry · doi:10.1038/nchem.1113 · Cited by 405

Practical chiral alcohol manufacture using ketoreductases

Huisman, G. W., Liang, J., & Krebber, A. (2010) · Current Opinion in Chemical Biology · doi:10.1016/j.cbpa.2009.12.003 · Cited by 398

Biocatalysis — key to sustainable industrial chemistry

Wohlgemuth, R. (2010) · Current Opinion in Biotechnology · doi:10.1016/j.copbio.2010.09.016 · Cited by 334

Asymmetric bioreduction of activated C=C bonds using enoate reductases from the old yellow enzyme family

Stuermer, R., Hauer, B., Hall, M., & Faber, K. (2007) · Current Opinion in Chemical Biology · doi:10.1016/j.cbpa.2007.02.025 · Cited by 330

Synthesis of chiral pharmaceutical intermediates by biocatalysis

Patel, R. N. (2008) · Coordination Chemistry Reviews · doi:10.1016/j.ccr.2007.10.031 · Cited by 329

Ionic liquids in biotransformations: from proof-of-concept to emerging deep-eutectic-solvents

Domínguez de María, P., & Maugeri, Z. (2011) · Current Opinion in Chemical Biology · doi:10.1016/j.cbpa.2010.11.008 · Cited by 314

Cytochrome P450: taming a wild type enzyme

Jung, S. T., Lauchli, R., & Arnold, F. H. (2011) · Current Opinion in Biotechnology · doi:10.1016/j.copbio.2011.02.008 · Cited by 293

Cytochromes P450 as useful biocatalysts: addressing the limitations

O'Reilly, E., Köhler, V., Flitsch, S. L., & Turner, N. J. (2011) · Chemical Communications · doi:10.1039/c0cc03165h · Cited by 277

Toward advanced ionic liquids. Polar, enzyme-friendly solvents for biocatalysis

Gorke, J., Srienc, F., & Kazlauskas, R. (2010) · Biotechnology and Bioprocess Engineering · doi:10.1007/s12257-009-3079-z · Cited by 273

Recent Developments in Lipase‐Catalyzed Synthesis of Polyesters

Kobayashi, S. (2009) · Macromolecular Rapid Communications · doi:10.1002/marc.200800690 · Cited by 270

Development of a Chemoenzymatic Manufacturing Process for Pregabalin

Martinez, C. A., Hu, S., Dumond, Y., Tao, J., Kelleher, P., & Tully, L. (2008) · Organic Process Research & Development · doi:10.1021/op7002248 · Cited by 245

Process considerations for the asymmetric synthesis of chiral amines using transaminases

Tufvesson, P., Lima‐Ramos, J., Jensen, J. S., Al‐Haque, N., Neto, W., & Woodley, J. M. (2011) · Biotechnology and Bioengineering · doi:10.1002/bit.23154 · Cited by 241

Biocatalysis in development of green pharmaceutical processes

Tao, J., & Xu, J.-H. (2009) · Current Opinion in Chemical Biology · doi:10.1016/j.cbpa.2009.01.018 · Cited by 236

Whole-cell biocatalysts for biodiesel fuel production

Fukuda, H., Hama, S., Tamalampudi, S., & Noda, H. (2008) · Trends in Biotechnology · doi:10.1016/j.tibtech.2008.08.001 · Cited by 235

Enzyme-catalysis breathes new life into polyester condensation polymerizations

Gross, R. A., Ganesh, M., & Lu, W. (2010) · Trends in Biotechnology · doi:10.1016/j.tibtech.2010.05.004 · Cited by 233

Recent Developments in the Application of Baeyer–Villiger Monooxygenases as Biocatalysts

de Gonzalo, G., Mihovilovic, M. D., & Fraaije, M. W. (2010) · ChemBioChem · doi:10.1002/cbic.201000395 · Cited by 224

Status of protein engineering for biocatalysts: how to design an industrially useful biocatalyst

Bommarius, A. S., Blum, J. K., & Abrahamson, M. J. (2010) · Current Opinion in Chemical Biology · doi:10.1016/j.cbpa.2010.11.011 · Cited by 218

A Novel Semi-biosynthetic Route for Artemisinin Production Using Engineered Substrate-Promiscuous P450 BM3

Dietrich, J. A., Yoshikuni, Y., Fisher, K. J., Woolard, F. X., Ockey, D., McPhee, D. J., Renninger, N. S., Chang, M. C. Y., Baker, D., & Keasling, J. D. (2009) · ACS Chemical Biology · doi:10.1021/cb900006h · Cited by 186

Transformation of steroids by actinobacteria: a review

Donova, M. V. (2007) · Applied Biochemistry and Microbiology · doi:10.1134/s0003683807010012 · Cited by 179

Enzymes in neoteric solvents: From one-phase to multiphase systems

Lozano, P. (2010) · Green Chemistry · doi:10.1039/b919088k · Cited by 178

Developments and trends in enzyme catalysis in nonconventional media

Hari Krishna, S. (2002) · Biotechnology Advances · doi:10.1016/s0734-9750(02)00019-8 · Cited by 177

Optimization of the In-Silico-Designed Kemp Eliminase KE70 by Computational Design and Directed Evolution

Khersonsky, O., Röthlisberger, D., Wollacott, A. M., Murphy, P., Dym, O., Albeck, S., Kiss, G., Houk, K. N., Baker, D., & Tawfik, D. S. (2011) · Journal of Molecular Biology · doi:10.1016/j.jmb.2011.01.041 · Cited by 177

Cradle-to-gate environmental assessment of enzyme products produced industrially in denmark by novozymes A/S

Nielsen, P. H., Oxenbøll, K. M., & Wenzel, H. (2007) · The International Journal of Life Cycle Assessment · doi:10.1007/s11367-006-2651-4 · Cited by 173

Benchmark Reaction Rates, the Stability of Biological Molecules in Water, and the Evolution of Catalytic Power in Enzymes

Wolfenden, R. (2011) · Annual Review of Biochemistry · doi:10.1146/annurev-biochem-060409-093051 · Cited by 164

Asymmetric Self‐ and Cross‐Aldol Reactions of Glycolaldehyde Catalyzed by D ‐Fructose‐6‐phosphate Aldolase

Garrabou, X., Castillo, J. A., Guérard‐Hélaine, C., Parella, T., Joglar, J., Lemaire, M., & Clapés, P. (2009) · Angewandte Chemie International Edition · doi:10.1002/anie.200902065 · Cited by 147

Biocatalytic reactions in hydrophobic ionic liquids

Sureshkumar, M., & Lee, C. (2009) · Journal of Molecular Catalysis B Enzymatic · doi:10.1016/j.molcatb.2009.03.008 · Cited by 143

Bacterial Lipases as Potential Industrial Biocatalysts: An Overview

Sangeetha, R., Arulpandi, I., & Geetha, A. (2011) · Research Journal of Microbiology · doi:10.3923/jm.2011.1.24 · Cited by 142

Enzymatic Asymmetric Synthesis of Enantiomerically Pure Aliphatic, Aromatic and Arylaliphatic Amines with (R)‐Selective Amine Transaminases

Schätzle, S., Steffen‐Munsberg, F., Thontowi, A., Höhne, M., Robins, K. T., & Bornscheuer, U. T. (2011) · Advanced Synthesis & Catalysis · doi:10.1002/adsc.201100435 · Cited by 131

P450 Fingerprinting Method for Rapid Discovery of Terpene Hydroxylating P450 Catalysts with Diversified Regioselectivity

Zhang, K., Damaty, S. E., & Fasan, R. (2011) · Journal of the American Chemical Society · doi:10.1021/ja109590h · Cited by 122

Use of Enzymes in the Production of Semi-Synthetic Penicillins and Cephalosporins: Drawbacks and Perspectives

Volpato, G. Q., Rodrigues, R. C., & Fernández‐Lafuente, R. (2010) · Current Medicinal Chemistry · doi:10.2174/092986710793205435 · Cited by 121

D ‐Fructose‐6‐phosphate Aldolase in Organic Synthesis: Cascade Chemical‐Enzymatic Preparation of Sugar‐Related Polyhydroxylated Compounds

Concia, A. L., Lozano, C., Castillo, J. A., Parella, T., Joglar, J., & Clapés, P. (2009) · Chemistry - A European Journal · doi:10.1002/chem.200802532 · Cited by 117

Yeast cell factories for fine chemical and API production

Pscheidt, B., & Glieder, A. (2008) · Microbial Cell Factories · doi:10.1186/1475-2859-7-25 · Cited by 116

Combinatorial Alanine Substitution Enables Rapid Optimization of Cytochrome P450BM3 for Selective Hydroxylation of Large Substrates

Lewis, J. C., Mantovani, S. M., Fu, Y., Snow, C. D., Komor, R. S., Wong, C., & Arnold, F. H. (2010) · ChemBioChem · doi:10.1002/cbic.201000565 · Cited by 115

Directed Evolution of Enantioselective Enzymes: An Unconventional Approach to Asymmetric Catalysis in Organic Chemistry

Reetz, M. T. (2009) · The Journal of Organic Chemistry · doi:10.1021/jo901046k · Cited by 100

‘Designer reagents’ recombinant microorganisms: new and powerful tools for organic synthesis

Kayser, M. M. (2008) · Tetrahedron · doi:10.1016/j.tet.2008.10.039 · Cited by 97

Enzymes for pharmaceutical applications—a cradle-to-gate life cycle assessment

Kim, S., Jiménez‐González, C., & Dale, B. E. (2009) · The International Journal of Life Cycle Assessment · doi:10.1007/s11367-009-0081-9 · Cited by 91

The Substrate Spectra of Pentaerythritol Tetranitrate Reductase, Morphinone Reductase, N‐Ethylmaleimide Reductase and Estrogen‐Binding Protein in the Asymmetric Bioreduction of Activated Alkenes

Mueller, N. J., Stueckler, C., Hauer, B., Baudendistel, N., Housden, H. R., Bruce, N. C., & Faber, K. (2010) · Advanced Synthesis & Catalysis · doi:10.1002/adsc.200900832 · Cited by 86

Biocatalytic Access to α,α‐Dialkyl‐α‐amino Acids by a Mechanism‐Based Approach

Fesko, K., Uhl, M. K., Steinreiber, J., Gruber, K. F., & Griengl, H. (2009) · Angewandte Chemie International Edition · doi:10.1002/anie.200904395 · Cited by 81

PEER REVIEW ORIGINAL RESEARCH: EHS & LCA assessment for 7-ACA synthesis A case study for comparing biocatalytic & chemical synthesis

Henderson, R. K., Jiménez‐González, C., Preston, C., Constable, D. J. C., & Woodley, J. M. (2008) · Industrial Biotechnology · doi:10.1089/ind.2008.4.180 · Cited by 78

Whole cell biocatalysis in nonconventional media

Nikolova, P. V., & Ward, O. P. (1993) · Journal of Industrial Microbiology & Biotechnology · doi:10.1007/bf01569905 · Cited by 77

A new nitrilase from Bradyrhizobium japonicum USDA 110

Zhu, D., Mukherjee, C., Yang, Y., Rios, B. E., Gallagher, D. T., Smith, N. N., Biehl, E. R., & Hua, L. (2007) · Journal of Biotechnology · doi:10.1016/j.jbiotec.2007.10.001 · Cited by 75

A new method to increase selectivity of transglutaminase mediated PEGylation of salmon calcitonin and human growth hormone

Mero, A., Schiavon, M., Veronese, F. M., & Pasut, G. (2011) · Journal of Controlled Release · doi:10.1016/j.jconrel.2011.04.024 · Cited by 73

Converting an Esterase into an Epoxide Hydrolase

Jochens, H., Stiba, K., Savile, C. K., Fujii, R., Yu, J., Gerassenkov, T., Kazlauskas, R. J., & Bornscheuer, U. T. (2009) · Angewandte Chemie International Edition · doi:10.1002/anie.200806276 · Cited by 71

Strategies for discovery and improvement of enzyme function: state of the art and opportunities

Kaul, P., & Asano, Y. (2011) · Microbial Biotechnology · doi:10.1111/j.1751-7915.2011.00280.x · Cited by 70

An Efficient Route to Selective Bio‐oxidation Catalysts: an Iterative Approach Comprising Modeling, Diversification, and Screening, Based on CYP102A1

Seifert, A., Antonovici, M., Hauer, B., & Pleiss, J. (2011) · ChemBioChem · doi:10.1002/cbic.201100067 · Cited by 69

Investigation of lipase-catalyzed Michael-type carbon–carbon bond formations

Strohmeier, G. A., Sović, T., Steinkellner, G., Hartner, F. S., Andryushkova, A., Purkarthofer, T., Glieder, A., Gruber, K. F., & Griengl, H. (2009) · Tetrahedron · doi:10.1016/j.tet.2009.05.042 · Cited by 65

Lipase-Catalyzed Synthesis of Aliphatic Polyesters via Copolymerization of Lactone, Dialkyl Diester, and Diol

Jiang, Z. (2008) · Biomacromolecules · doi:10.1021/bm800814m · Cited by 64

Synthesis of Aliphatic (S)‐α‐Hydroxycarboxylic Amides using a One‐Pot Bienzymatic Cascade of Immobilised Oxynitrilase and Nitrile Hydratase

van Pelt, S., van Rantwijk, F., & Sheldon, R. A. (2009) · Advanced Synthesis & Catalysis · doi:10.1002/adsc.200800625 · Cited by 62

Fungal nitrilases as biocatalysts: Recent developments

Martı́nková, L., Vejvoda, V., Kaplan, O., Kubáč, D., Malandra, A., Cantarella, M., Bezouška, K., & Křen, V. (2009) · Biotechnology Advances · doi:10.1016/j.biotechadv.2009.04.027 · Cited by 60

Lipase-Catalyzed Synthesis of Aliphatic Poly(carbonate-co-esters)

Jiang, Z., Liu, C., & Gross, R. A. (2008) · Macromolecules · doi:10.1021/ma702868a · Cited by 56

Direct Enzymatic Synthesis of a Polyester with Free Pendant Mercapto Groups

Katô, M., Toshima, K., & Matsumura, S. (2008) · Biomacromolecules · doi:10.1021/bm801132d · Cited by 55

Discovery of a mandelonitrile hydrolase from Bradyrhizobium japonicum USDA110 by rational genome mining

Zhu, D., Mukherjee, C., Biehl, E. R., & Hua, L. (2007) · Journal of Biotechnology · doi:10.1016/j.jbiotec.2007.02.001 · Cited by 54

Rational redesign of Candida antarctica lipase B for the ring opening polymerization of d,d-lactide

Takwa, M., Larsen, M. W., Hult, K., & Martinelle, M. (2011) · Chemical Communications · doi:10.1039/c1cc10865d · Cited by 50

Biocatalytic synthesis of polyesters from sugar-based building blocks using immobilized Candida antarctica lipase B

Habeych, D. I., Juhl, P. B., Pleiss, J., Vanegas, D. C., Eggink, G., & Boeriu, C. G. (2011) · Journal of Molecular Catalysis B Enzymatic · doi:10.1016/j.molcatb.2011.02.015 · Cited by 44

Enzymatic acylation of levoglucosan in acetonitrile and ionic liquids

Galletti, P., Moretti, F., Samorì, C., & Tagliavini, E. (2007) · Green Chemistry · doi:10.1039/b702031g · Cited by 44

Synthesis of organosiloxane copolymers using enzymatic polyesterification

Poojari, Y., Palsule, A. S., Cai, M., Clarson, S. J., & Gross, R. A. (2008) · European Polymer Journal · doi:10.1016/j.eurpolymj.2008.07.043 · Cited by 42

Nitrilases Catalyze Key Step to Conformationally Constrained GABA Analogous γ-Amino Acids in High Optical Purity

Winkler, M., Knall, A. C., Kulterer, M. R., & Klempier, N. (2007) · The Journal of Organic Chemistry · doi:10.1021/jo070776j · Cited by 39

A highly efficient ADH‐coupled NADH‐recycling system for the asymmetric bioreduction of carbon‐carbon double bonds using enoate reductases

Tauber, K., Hall, M., Kroutil, W., Fabian, W. M. F., Faber, K., & Glueck, S. M. (2011) · Biotechnology and Bioengineering · doi:10.1002/bit.23078 · Cited by 37

Kinetic Analysis of L ‐Carnosine Formation by β‐Aminopeptidases

Heck, T., Makam, V. S., Lutz, J., Blank, L. M., Schmid, A., Seebàch, D., Kohler, H. E., & Geueke, B. (2010) · Advanced Synthesis & Catalysis · doi:10.1002/adsc.200900697 · Cited by 30

Promiscuous enzyme-catalyzed regioselective Michael addition of purine derivatives to α,β-unsaturated carbonyl compounds in organic solvent

Wang, J., Xu, J., Wu, Q., Lv, D., & Lin, X.-F. (2009) · Tetrahedron · doi:10.1016/j.tet.2009.01.056 · Cited by 28

Enzyme activity evaluation of organic solvent‐treated phenylalanine ammonia lyase

Quinn, A. J., Pickup, M. J., & D’Cunha, G. B. (2011) · Biotechnology Progress · doi:10.1002/btpr.687 · Cited by 13

Deep Eutectic Solvents (DESs) and Their Applications

Smith, E. L., Abbott, A. P., & Ryder, K. S. (2014) · Chemical Reviews · doi:10.1021/cr300162p · Cited by 7,378

Enzyme immobilisation in biocatalysis: why, what and how

Sheldon, R. A., & van Pelt, S. (2013) · Chem. Soc. Rev. · doi:10.1039/c3cs60075k · Cited by 2,675

Natural Deep Eutectic Solvents – Solvents for the 21st Century

Paiva, A., Craveiro, R., Aroso, I., Martins, M., Reis, R. L., & Duarte, A. R. C. (2014) · ACS Sustainable Chemistry & Engineering · doi:10.1021/sc500096j · Cited by 2,458

Are Deep Eutectic Solvents Useful in Chromatography? A Short Review

Płotka-Wasylka, J., Rutkowska, M., & de la Guardia, M. (2021) · Journal of Chromatography A · doi:10.1016/j.chroma.2021.461918 · Cited by 51