Biocatalysis for Practitioners
Gonzalo, Gonzalo de, Iván Lavandera
Abstract
Kinetic Resolution and Deracemization 150 6.3.2Practical Examples with Amine Oxidases 151 6.3.2.1 One-pot, One-enzyme Oxidative Pictet-Spengler Approach Combined with Deracemization 151 6.3.2.2 Desymmetrization of meso-compounds 152 6.4 Transaminases (or Aminotransferases) 152 6.4.1 Practical Approaches with Transaminases 153 6.4.2Practical Examples with Transaminases 153 6.4.2.1 Kinetic Resolution and Deracemization 153 6.4.2.2 Asymmetric Synthesis from Prochiral Ketone 155 6.5 Amine Dehydrogenases, Imine Reductases, and Reductive Aminases 155 6.5.1 Practical Approaches with Amine Dehydrogenases, Imine Reductases, and Reductive Aminases 156 6.5.2Practical Examples with Amine Dehydrogenases, Imine Reductases, and Reductive Aminases 160 6.5.2.1 IRed-Catalyzed Reductive Amination of an Aldehyde Combined with KR of a Racemic Amine 160 6.5.2.2 Asymmetric Reductive Amination Catalyzed by AmDH 162 6.6 Ammonia Lyases 162 6.6.1 Practical Approaches with Ammonia Lyases 163 6.6.1.1Aspartase, 3-Methylaspartate Ammonia Lyase, and Related Enzymes 163 6.6.1.2Aromatic Amino Acid Ammonia Lyases and Mutases 165 6.6.2Practical Examples with Ammonia Lyases 166 6.6.2.1 Chemoenzymatic Synthesis of (S)-2-Indolinecarboxylic Acid 166 6.6.2.2 Synthesis of L-Aspartate from Fumarate 166 6.6.2.3 Enzymatic and Chemoenzymatic Synthesis of Toxin A and Aspergillomarasmine A and B 166 6.7 Pictet-Spenglerases 167 6.7.1 Practical Approaches with Pictet-Spenglerases 167 6.7.2 Practical Examples with Pictet-Spenglerases 169 6.7.2.1 Biocatalytic Synthesis of (R)-Harmicine 169 6.7.2.2 Biocatalytic Synthesis of (S)-Trolline and Analogs 169 6.8 Engineered Cytochrome P450s (Cytochrome "P411") 169 6.8.1 Practical Approaches with Engineered Cytochrome P450s 170 6.9Protocols for Selected Reactions 171 6.9.1 Hydrolases 171 6.9.1.1Kinetic Resolution rac-Methylbenzylamine (rac-1) 171 6.9.1.2Dynamic Kinetic Resolution of Norsertraline Intermediate (rac-3) 171 6.9.2 Monoamine Oxidases 172 6.9.2.1 Chemoenzymatic Deracemization of Harmicine (rac-8) 172 6.9.3 ω-Transaminases 172 6.9.3.1 Deracemization of Mexiletine (rac-9, Kinetic Resolution, Followed by Formal Reductive Amination) 172 6.9.4Imine Reductases and Amine Dehydrogenases 172 6.9.4.1Reductive Amination of Aldehyde (11) with Kinetic Resolution of Amine Nucleophile (rac-trans-12) 172