期刊
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
卷 53, 期 51, 页码 14153-14157出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201409227
关键词
bioorganic chemistry; enzyme catalysis; ester formation; lactone opening; nylon-6
资金
- European Commission [245144, THEME KBBE-2009-3-3-02]
- Austrian BMWFW
- BMVIT
- SFG
- Standortagentur Tirol
- ZIT through Austrian FFG-COMET-Funding Program
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.
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