Shortening Synthetic Routes to Small Molecule Active Pharmaceutical Ingredients Employing Biocatalytic Methods
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Title
Shortening Synthetic Routes to Small Molecule Active Pharmaceutical Ingredients Employing Biocatalytic Methods
Authors
Keywords
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Journal
CHEMICAL REVIEWS
Volume 122, Issue 1, Pages 1052-1126
Publisher
American Chemical Society (ACS)
Online
2021-12-01
DOI
10.1021/acs.chemrev.1c00574
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- Nitrile as Activating Group in the Asymmetric Bioreduction of β-Cyanoacrylic Acids Catalyzed by Ene-Reductases
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- Enantioselective Allylation of Thiophene-2-carbaldehyde: Formal Total Synthesis of Duloxetine
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- Cytochromes P450 as promising catalysts for biotechnological application: chances and limitations
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- Efficient production of ethyl (R)-2-hydroxy-4-phenylbutyrate using a cost-effective reductase expressed in Pichia pastoris
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- Bioreductions Catalyzed by an Alcohol Dehydrogenase in Non-aqueous Media
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- New developments in ‘ene’-reductase catalysed biological hydrogenations
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- Comprehensive mass analysis for chemical processes, a case study on l-Dopa manufacture
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- Pregabalinâs abuse potential: a mini review focusing on the pharmacological profile
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- 4′-Ethynyl-2-fluoro-2′-deoxyadenosine (EFdA) Inhibits HIV-1 Reverse Transcriptase with Multiple Mechanisms
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- Conception and Evolution of Stereocontrolled Strategies toward Functionalized 8-Aryloctanoic Acids Related to the Total Synthesis of Aliskiren
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- Total synthesis of fluoxetine and duloxetine through an in situ imine formation/borylation/transimination and reduction approach
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- A Highly Efficient Asymmetric Synthesis of Vernakalant
- (2014) John Limanto et al. ORGANIC LETTERS
- Development of a Concise, Asymmetric Synthesis of a Smoothened Receptor (SMO) Inhibitor: Enzymatic Transamination of a 4-Piperidinone with Dynamic Kinetic Resolution
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- Development of a Biocatalytic Process to Prepare (S)-N-Boc-3-hydroxypiperidine
- (2014) Xin Ju et al. ORGANIC PROCESS RESEARCH & DEVELOPMENT
- Development of a Practical, Biocatalytic Reduction for the Manufacture of (S)-Licarbazepine Using an Evolved Ketoreductase
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- Enzymatic asymmetric synthesis of the silodosin amine intermediate
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- Identification of promiscuous ene-reductase activity by mining structural databases using active site constellations
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- Synthesis of ethyl (R)-4-cyano-3-hydroxybutyrate in high concentration using a novel halohydrin dehalogenase HHDH-PL from Parvibaculum lavamentivorans DS-1
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- Systematic Review: Comparative Effectiveness of Angiotensin-Converting Enzyme Inhibitors and Angiotensin II Receptor Blockers for Treating Essential Hypertension
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- Chemical and enzymatic approaches to the synthesis of optically pure ethyl (R)-4-cyano-3-hydroxybutanoate
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- On the development of new biocatalytic processes for practical pharmaceutical synthesis
- (2013) Gjalt W Huisman et al. CURRENT OPINION IN CHEMICAL BIOLOGY
- CC bond formation using ThDP-dependent lyases
- (2013) Michael Müller et al. CURRENT OPINION IN CHEMICAL BIOLOGY
- Chemoenzymatic Synthesis of Enantiomerically Puresyn-Configured 1-Aryl-3-methylisochroman Derivatives
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- Scalable biocatalytic synthesis of optically pure ethyl (R)-2-hydroxy-4-phenylbutyrate using a recombinant E. coli with high catalyst yield
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- Chemoenzymatic Asymmetric Synthesis of Pregabalin Precursors via Asymmetric Bioreduction of β-Cyanoacrylate Esters Using Ene-Reductases
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- Total Synthesis of Ezetimibe, a Cholesterol Absorption Inhibitor
- (2013) Marcin Śnieżek et al. JOURNAL OF ORGANIC CHEMISTRY
- Engineering an Enantioselective Amine Oxidase for the Synthesis of Pharmaceutical Building Blocks and Alkaloid Natural Products
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- Consensus and Update on the Definition of On-Treatment Platelet Reactivity to Adenosine Diphosphate Associated With Ischemia and Bleeding
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- Highly Efficient Synthesis of (R)-3-Quinuclidinol in a Space–Time Yield of 916 g L–1 d–1 Using a New Bacterial Reductase ArQR
- (2013) Wen-Xia Zhang et al. ORGANIC LETTERS
- Enzyme-Catalyzed Hydrolysis of Bicycloheptane and Cyclobutene Diesters to Monoesters
- (2013) Zhiwei Guo et al. ORGANIC PROCESS RESEARCH & DEVELOPMENT
- Efficient Synthesis of (S)-1-(5-Fluoropyrimidin-2-yl)ethylamine Using an ω-Transaminase Biocatalyst in a Two-Phase System
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- Use of ω-Transaminase Enzyme Chemistry in the Synthesis of a JAK2 Kinase Inhibitor
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- Process Development of C–N Cross-Coupling and Enantioselective Biocatalytic Reactions for the Asymmetric Synthesis of Niraparib
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- Asymmetric Preparation of prim-, sec-, and tert-Amines Employing Selected Biocatalysts
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- A Highly Productive, Whole-Cell DERA Chemoenzymatic Process for Production of Key Lactonized Side-Chain Intermediates in Statin Synthesis
- (2013) Matej Ošlaj et al. PLoS One
- The Value of Neuraminidase Inhibitors for the Prevention and Treatment of Seasonal Influenza: A Systematic Review of Systematic Reviews
- (2013) Barbara Michiels et al. PLoS One
- An efficient synthesis for eslicarbazepine acetate, oxcarbazepine, and carbamazepine
- (2013) B. Ravinder et al. TETRAHEDRON LETTERS
- Biocatalytic Approaches to the Synthesis of Enantiomerically Pure Chiral Amines
- (2013) Diego Ghislieri et al. TOPICS IN CATALYSIS
- Stereospecific Reduction of Methyl o-Chlorobenzoylformate at 300 g⋅L−1 without Additional Cofactor using a Carbonyl Reductase Mined from Candida glabrata
- (2012) Hongmin Ma et al. ADVANCED SYNTHESIS & CATALYSIS
- Ene Reductase-Catalysed Synthesis of (R)-Profen Derivatives
- (2012) Jörg Pietruszka et al. ADVANCED SYNTHESIS & CATALYSIS
- Properties and biotechnological applications of halohydrin dehalogenases: current state and future perspectives
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- Recent Lipase-Catalyzed Hydrolytic Approaches to Pharmacologically Important β-and γ-Amino Acids
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- Asymmetric bioreduction of activated alkenes to industrially relevant optically active compounds
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- CRTH2 Antagonist MK-7246: A Synthetic Evolution from Discovery through Development
- (2012) Carmela Molinaro et al. JOURNAL OF ORGANIC CHEMISTRY
- Efficient, Chemoenzymatic Process for Manufacture of the Boceprevir Bicyclic [3.1.0]Proline Intermediate Based on Amine Oxidase-Catalyzed Desymmetrization
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- Engineering the third wave of biocatalysis
- (2012) U. T. Bornscheuer et al. NATURE
- Enantioselective Synthesis of a Dual Orexin Receptor Antagonist
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- Corey–Itsuno Reduction of Ketones: A Development of Safe and Inexpensive Process for Synthesis of Some API Intermediates
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- Convergent Kilogram-Scale Synthesis of Dual Orexin Receptor Antagonist
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- Redesigning and characterizing the substrate specificity and activity of Vibrio fluvialis aminotransferase for the synthesis of imagabalin
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- Bioreduction of methyl o-chlorobenzoylformate at 500gL−1 without external cofactors for efficient production of enantiopure clopidogrel intermediate
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- Tuning P450 Enzymes as Oxidation Catalysts
- (2012) Rudi Fasan ACS Catalysis
- Catalytic and Structural Features of Flavoprotein Hydroxylases and Epoxidases
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- Stereoselectivity of Four (R)-Selective Transaminases for the Asymmetric Amination of Ketones
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- Multi-Enzymatic Cascade Reactions: Overview and Perspectives
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- Highly efficient synthesis of chiral alcohols with a novel NADH-dependent reductase from Streptomyces coelicolor
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- Industrial biotransformations in the synthesis of building blocks leading to enantiopure drugs
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- Asymmetric Synthesis of (S)-2-Indolinecarboxylic Acid by Combining Biocatalysis and Homogeneous Catalysis
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- Cytochromes P450 as useful biocatalysts: addressing the limitations
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- C−C Bond-Forming Lyases in Organic Synthesis
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- Cytochrome P450: taming a wild type enzyme
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- Regulation of Immune Responses by Prostaglandin E2
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- Design, Synthesis, Radiolabeling, and in Vitro and in Vivo Evaluation of Bridgehead Iodinated Analogues ofN-{2-[4-(2-Methoxyphenyl)piperazin-1-yl]ethyl}-N-(pyridin-2-yl)cyclohexanecarboxamide (WAY-100635) as Potential SPECT Ligands for the 5-HT1AReceptor
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- Several Generations of Chemoenzymatic Synthesis of Oseltamivir (Tamiflu): Evolution of Strategy, Quest for a Process-Quality Synthesis, and Evaluation of Efficiency Metrics
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- A Formal Synthesis of Ezetimibe via Cycloaddition/Rearrangement Cascade Reaction
- (2011) Michał Michalak et al. JOURNAL OF ORGANIC CHEMISTRY
- Stereoselective Amination of Chiral Benzylic Ethers Using Chlorosulfonyl Isocyanate: Total Synthesis of (+)-Sertraline
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- Direct Catalytic Enantio- and Diastereoselective Aldol Reaction of Thioamides
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- Reaction Development and Mechanistic Study of a Ruthenium Catalyzed Intramolecular Asymmetric Reductive Amination en Route to the Dual Orexin Inhibitor Suvorexant (MK-4305)
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- Pharmacological characterization of MK-6096 – A dual orexin receptor antagonist for insomnia
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- Enantioselective Total Synthesis of the Potent Anti-HIV Nucleoside EFdA
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- Biotechnological Development of a Practical Synthesis of Ethyl (S)-2-Ethoxy-3-(p-methoxyphenyl)propanoate (EEHP): Over 100-Fold Productivity Increase from Yeast Whole Cells to Recombinant Isolated Enzymes
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- Multikilogram-Scale Synthesis of a Chiral Cyclopropanol and an Investigation of the Safe Use of Lithium Acetylide–Ethylene Diamine Complex
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- Commercial Synthesis of (S,S)-Reboxetine Succinate: A Journey To Find the Cheapest Commercial Chemistry for Manufacture
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- Development of an Improved Immobilized CAL-B for the Enzymatic Resolution of a Key Intermediate to Odanacatib
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- Fit-for-Purpose Development of the Enabling Route to Crizotinib (PF-02341066)
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- LCZ696: a dual-acting sodium supramolecular complex
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- Recent developments in the asymmetric hydrolytic ring opening of epoxides catalysed by microbial epoxide hydrolase
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- Discovery of MK-7246, a selective CRTH2 antagonist for the treatment of respiratory diseases
- (2010) Michel Gallant et al. BIOORGANIC & MEDICINAL CHEMISTRY LETTERS
- Chemoenzymatic asymmetric total synthesis of (S)-Rivastigmine using ω-transaminases
- (2010) Michael Fuchs et al. CHEMICAL COMMUNICATIONS
- A new dehydrogenase from Clostridium acetobutylicum for asymmetric synthesis: dynamic reductive kinetic resolution entry into the Taxotère side chain
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- Chemical Synthesis of Heterocyclic−Sugar Nucleoside Analogues
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- Calcitonin Gene-Related Peptide (CGRP) Receptor Antagonists in the Treatment of Migraine
- (2010) Paul L. Durham et al. CNS DRUGS
- Recent progress in stereoselective synthesis with aldolases
- (2010) Pere Clapés et al. CURRENT OPINION IN CHEMICAL BIOLOGY
- Practical chiral alcohol manufacture using ketoreductases
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- Ammonia lyases and aminomutases as biocatalysts for the synthesis of α-amino and β-amino acids
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- Newer antibacterial drugs for a new century
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- Vernakalant
- (2010) Dobromir Dobrev et al. NATURE REVIEWS DRUG DISCOVERY
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- Biocatalytic Resolution of Bis-tetrahydrofuran Alcohol
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- Biocatalytic Asymmetric Synthesis of Chiral Amines from Ketones Applied to Sitagliptin Manufacture
- (2010) C. K. Savile et al. SCIENCE
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- (2010) P. K. Ajikumar et al. SCIENCE
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- (2010) Vincent Soriano Therapeutics and Clinical Risk Management
- Mechanism of the Asymmetric Sulfoxidation in the Esomeprazole Process: Effects of the Imidazole Backbone for the Enantioselection
- (2009) Muthu Seenivasaperumal et al. ADVANCED SYNTHESIS & CATALYSIS
- Short Chemoenzymatic Azide-Free Synthesis of Oseltamivir (Tamiflu): Approaching the Potential for Process Efficiency
- (2009) Lukas Werner et al. ADVANCED SYNTHESIS & CATALYSIS
- Symmetry-Based Design for the Chemoenzymatic Synthesis of Oseltamivir (Tamiflu) from Ethyl Benzoate
- (2009) Bradford Sullivan et al. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
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- (2009) Javier Barrios-González et al. APPLIED MICROBIOLOGY AND BIOTECHNOLOGY
- Microbial cells as catalysts for stereoselective red–ox reactions
- (2009) J.D. Carballeira et al. BIOTECHNOLOGY ADVANCES
- Transaminase-catalyzed asymmetric synthesis of l-2-aminobutyric acid from achiral reactants
- (2009) Jong-Shik Shin et al. BIOTECHNOLOGY LETTERS
- Biocatalytic Routes to Optically Active Amines
- (2009) Matthias Höhne et al. ChemCatChem
- Biocatalytic carboxylation
- (2009) Silvia M. Glueck et al. CHEMICAL SOCIETY REVIEWS
- Boceprevir, an NS3 Protease Inhibitor of HCV
- (2009) Kenneth Berman et al. Clinics in Liver Disease
- Biocatalysis in development of green pharmaceutical processes
- (2009) Junhua Tao et al. CURRENT OPINION IN CHEMICAL BIOLOGY
- Hydroxylation of l-proline to cis-3-hydroxy-l-proline by recombinant Escherichia coli expressing a synthetic l-proline-3-hydroxylase gene
- (2009) Robert M. Johnston et al. ENZYME AND MICROBIAL TECHNOLOGY
- A green-by-design biocatalytic process for atorvastatin intermediate
- (2009) Steven K. Ma et al. GREEN CHEMISTRY
- Synthesis of 4-phenylpyrrolidin-2-one via dynamic kinetic resolution catalyzed by ω-transaminases
- (2009) Dominik Koszelewski et al. JOURNAL OF MOLECULAR CATALYSIS B-ENZYMATIC
- Ru-catalyzed enantioselective preparation of methyl (R)-o-chloromandelate and its application in the synthesis of (S)-Clopidogrel
- (2009) Lu Yin et al. JOURNAL OF ORGANOMETALLIC CHEMISTRY
- Highly Efficient Asymmetric Synthesis of Sitagliptin
- (2009) Karl B. Hansen et al. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
- Deracemization of Mexiletine Biocatalyzed by ω-Transaminases
- (2009) Dominik Koszelewski et al. ORGANIC LETTERS
- Enzymatic Desymmetrization of Dimethyl Cylcohex-4-ene-cis-1,2-dicarboxylate to (1S,2R)-2-(Methoxycarbonyl)cyclohex-4-ene-1-carboxylic Acid
- (2009) Animesh Goswami et al. ORGANIC PROCESS RESEARCH & DEVELOPMENT
- An Improved and Scalable Process for the Synthesis of Ezetimibe: An Antihypercholesterolemia Drug†
- (2009) C. H. V. A. Sasikala et al. ORGANIC PROCESS RESEARCH & DEVELOPMENT
- Continuous Biocatalytic Processes
- (2009) Nagaraj N. Rao et al. ORGANIC PROCESS RESEARCH & DEVELOPMENT
- Routes for the Synthesis of (2S)-2-Methyltetrahydropyran-4-one from Simple Optically Pure Building Blocks
- (2009) Kevin R. Anderson et al. ORGANIC PROCESS RESEARCH & DEVELOPMENT
- Highly Enantioselective Reduction of a Small Heterocyclic Ketone: Biocatalytic Reduction of Tetrahydrothiophene-3-one to the Corresponding (R)-Alcohol
- (2009) Jack Liang et al. ORGANIC PROCESS RESEARCH & DEVELOPMENT
- Development of a Biocatalytic Process as an Alternative to the (−)-DIP-Cl-Mediated Asymmetric Reduction of a Key Intermediate of Montelukast
- (2009) Jack Liang et al. ORGANIC PROCESS RESEARCH & DEVELOPMENT
- Enantiocomplementary Enzymes: Classification, Molecular Basis for Their Enantiopreference, and Prospects for Mirror-Image Biotransformations
- (2008) Paul F. Mugford et al. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
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- (2008) Ulf Hanefeld et al. CHEMICAL SOCIETY REVIEWS
- Heme-iron oxygenases: powerful industrial biocatalysts?
- (2008) Mattijs K Julsing et al. CURRENT OPINION IN CHEMICAL BIOLOGY
- Esomeprazole
- (2008) Kate McKeage et al. DRUGS
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- (2008) Enikő Forró et al. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
- New, Efficient Synthesis of Oseltamivir Phosphate (Tamiflu) via Enzymatic Desymmetrization of ameso-1,3-Cyclohexanedicarboxylic Acid Diester
- (2008) Ulrich Zutter et al. JOURNAL OF ORGANIC CHEMISTRY
- Orchestration of Concurrent Oxidation and Reduction Cycles for Stereoinversion and Deracemisation ofsec-Alcohols
- (2008) Constance V. Voss et al. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
- Preparative Asymmetric Synthesis of 4,4-Dimethoxytetrahydro-2H-pyran-3-ol with a Ketone Reductase and in Situ Cofactor Recycling using Glucose Dehydrogenase
- (2008) Birgit Kosjek et al. ORGANIC PROCESS RESEARCH & DEVELOPMENT
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- (2008) Ronald L. Hanson et al. ORGANIC PROCESS RESEARCH & DEVELOPMENT
- Development of a Chemoenzymatic Manufacturing Process for Pregabalin
- (2008) Carlos A. Martinez et al. ORGANIC PROCESS RESEARCH & DEVELOPMENT
- Optimisation of stabilised Carboxylesterase NP for enantioselective hydrolysis of naproxen methyl ester
- (2008) Lucia Steenkamp et al. PROCESS BIOCHEMISTRY
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- (2007) Constance V. Voss et al. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
- Synthesis of antidepressant duloxetine via asymmetric transfer hydrogenation
- (2007) Shan Zhen He et al. CHINESE CHEMICAL LETTERS
- Synthesis of chiral pharmaceutical intermediates by biocatalysis
- (2007) Ramesh N. Patel COORDINATION CHEMISTRY REVIEWS
- Recent applications of biocatalysis in developing green chemistry for chemical synthesis at the industrial scale
- (2007) Ningqing Ran et al. GREEN CHEMISTRY
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- (2007) Manuela Hermann et al. JOURNAL OF BIOTECHNOLOGY
- Posaconazole (Noxafil, SCH 56592), a new azole antifungal drug, was a discovery based on the isolation and mass spectral characterization of a circulating metabolite of an earlier lead (SCH 51048)
- (2007) Amin A. Nomeir et al. JOURNAL OF MASS SPECTROMETRY
- The active site of hydroxynitrile lyase from Prunus amygdalus: Modeling studies provide new insights into the mechanism of cyanogenesis
- (2002) Ingrid Dreveny et al. PROTEIN SCIENCE
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