Introducing an In Situ Capping Strategy in Systems Biocatalysis To Access 6-Aminohexanoic acid
| Autor: | Philip Engel, Francesco G. Mutti, John M. Woodley, Johann H. Sattler, Jan Pfeffer, Michael Fuchs, Barbara Grischek, Wolfgang Kroutil |
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| Rok vydání: | 2014 |
| Předmět: |
chemistry.chemical_classification
Molecular Structure Chemistry Carboxylic acid Cyclohexanol Esterases General Medicine General Chemistry Cyclohexanols Catalysis Enzyme catalysis chemistry.chemical_compound Ammonia Monomer Nucleophile Liver Biocatalysis Aminocaproic Acid Organic chemistry Animals Methanol Horses |
| Zdroj: | Angewandte Chemie International Edition. 53:14153-14157 |
| ISSN: | 1433-7851 |
| DOI: | 10.1002/anie.201409227 |
| Popis: | The combination of two cofactor self-sufficient biocatalytic cascade modules allowed the successful transformation of cyclohexanol into the nylon-6 monomer 6-aminohexanoic acid at the expense of only oxygen and ammonia. A hitherto unprecedented carboxylic acid capping strategy was introduced to minimize the formation of the dead-end intermediate 6-hydroxyhexanoic acid. For this purpose, the precursor e-caprolactone was converted in aqueous medium in the presence of methanol into the corresponding methyl ester instead of the acid. Hence, it was shown for the first time that esterases--specifically horse liver esterase--can perform the selective ring-opening of e-caprolactone with a clear preference for methanol over water as the nucleophile. |
| Databáze: | OpenAIRE |
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