Hydrolysis and Formation of Epoxides

Spelberg, Jeffrey H. Lutje; Vries, E.J. de

doi:10.1002/9783527639861.ch9

Cited by 5 publications

References 252 publications

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Oxazolidinone Synthesis through Halohydrin Dehalogenase‐ Catalyzed Dynamic Kinetic Resolution

et al. 2015

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An efficient dynamic kinetic resolution protocolu sing as ingle enzyme is described. Both the kinetic resolution and substrate racemization are catalyzed by halohydrin dehalogenase from Agrobacterium radiobacter AD1 (HheC). The HheC-catalyzed reactiono fe pibromohydrin and 2bromomethyl-2-methyloxirane with sodium cyanate afforded 5-substituted 2-oxazolidinones in high yields (97% and 87%) and high optical purity( 89% and > 99% ee)i nt he presence of catalytic amounts of bromide ion. Thesec ompounds are valuable building blocks with diverse synthetic applications.

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Oxazolidinone Synthesis through Halohydrin Dehalogenase‐ Catalyzed Dynamic Kinetic Resolution

et al. 2015

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Halohydrin Dehalogenases and Their Potential in Industrial Application – A Viewpoint of Enzyme Reaction Engineering

et al. 2020

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At the moment, there are approx. 100 published papers investigating halohydrin dehalogenases from different aspects; enzymology, molecular biology and reactions they can catalyse. Unquestionably, these enzymes are of great importance and hold an immense potential due to the wide spectrum of different compounds that can be synthesized by their action. These compounds, such as chiral epoxides, β‐substituted alcohols, oxazolidinones etc., significantly enrich the chemist's toolbox and, moreover, open the possibility for the synthesis of even more complex compounds. Still, there are many unknowns, and it is the purpose of this work to demonstrate the possibilities and bottlenecks, in scientific sense, that could further help in broadening the applicative potential of these fascinating enzymes.

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Comparing Different Strategies in Directed Evolution of Enzyme Stereoselectivity: Single‐ versus Double‐Code Saturation Mutagenesis

Sun

Lonsdale

et al. 2016

ChemBioChem

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Saturation mutagenesis at sites lining the binding pockets of enzymes constitutes a viable protein engineering technique for enhancing or inverting stereoselectivity. Statistical analysis shows that oversamplin g in the screening step (the bottleneck) increases astronomically as the number of residues in the ran- domization site increases, which is the reason why reduced amino acid alphabets have been employed, in addition to splitting large sites into smaller ones. Limonene epoxide hydrolase (LEH) has previously served as the experimental plat- form in these methodological efforts, enabling comparisons between single-code saturation mutagenesis (SCSM) and triple-code saturation mutagenes is (TCSM); these employ either only one or three amino acids, respectively, as building blocks. In this study the comparative platform is extended by exploring the efficacy of double-code saturation mutagenesis (DCSM), in which the reduced amino acid alphabet consists of two members, chosen according to the principles of rational design on the basis of structural information. The hydrolytic desymmetrization of cyclohexene oxide is used as the model reaction, with formation of either (R,R)- or (S,S)-cyclohexane- 1,2-diol. DCSM proves to be clearly superior to the likewise tested SCSM, affording both R,R-andS,S-selective mutants. These variants are also good catalysts in reactions of further substrates. Docking computations reveal the basis of enantio- selectivity

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Hydrolysis and Formation of Epoxides

Cited by 5 publications

References 252 publications

Oxazolidinone Synthesis through Halohydrin Dehalogenase‐ Catalyzed Dynamic Kinetic Resolution

Oxazolidinone Synthesis through Halohydrin Dehalogenase‐ Catalyzed Dynamic Kinetic Resolution

Halohydrin Dehalogenases and Their Potential in Industrial Application – A Viewpoint of Enzyme Reaction Engineering

Comparing Different Strategies in Directed Evolution of Enzyme Stereoselectivity: Single‐ versus Double‐Code Saturation Mutagenesis

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