Studies on the Catalytic Promiscuity of Limonene Epoxide Hydrolases in the Non‐hydrolytic Ring Opening of 1,2‐Epoxides
| Autor: | Erica Elisa Ferrandi, Ivan Bassanini, Sergio Riva, Daniela Monti |
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| Rok vydání: | 2020 |
| Předmět: |
2-epoxides
Cyclohexanol 010402 general chemistry 01 natural sciences Biochemistry limonene epoxide hydrolases 1 Substrate Specificity Catalysis chemistry.chemical_compound Nucleophile Potassium thiocyanate Cyclohexenes Rhodococcus Organic chemistry Molecular Biology Epoxide Hydrolases biology 010405 organic chemistry Hydrolysis Organic Chemistry 0104 chemical sciences Kinetics chemistry Biocatalysis Mutagenesis Site-Directed Solvents biology.protein Epoxy Compounds Molecular Medicine Sodium azide Enzyme promiscuity Cyclohexene oxide |
| Zdroj: | ChemBioChem 21 (2020): 1868–1874. doi:10.1002/cbic.201900694 info:cnr-pdr/source/autori:Bassanini I.; Ferrandi E.E.; Monti D.; Riva S./titolo:Studies on the Catalytic Promiscuity of Limonene Epoxide Hydrolases in the Non-hydrolytic Ring Opening of 1,2-Epoxides/doi:10.1002%2Fcbic.201900694/rivista:ChemBioChem (Print)/anno:2020/pagina_da:1868/pagina_a:1874/intervallo_pagine:1868–1874/volume:21 |
| ISSN: | 1439-7633 1439-4227 |
| DOI: | 10.1002/cbic.201900694 |
| Popis: | The non-hydrolytic ring opening of 1,2-epoxides in the presence of limonene epoxide hydrolases (LEHs) and different nucleophiles has been investigated. Lyophilized, wild-type LEHs were tested in selected water-saturated organic solvents in the presence of cyclohexene oxide as substrate and different alcohols, thiols and primary amines as nucleophiles. Although the LEHs retained an appreciable catalytic activity under different reaction conditions, formation of the desired 1,2-substituted cyclohexanols was not observed. Alternatively, LEH variants incapable of performing the hydrolytic reaction were generated by site-directed mutagenesis and tested in aqueous media in the presence of different water-soluble nucleophiles and cyclohexene oxide. Under defined reaction conditions, an acceleration of up to about threefold of the spontaneous reaction rate was observed in the presence of sodium azide and potassium thiocyanate as nucleophiles. |
| Databáze: | OpenAIRE |
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