A multi-enzymatic cascade reaction for the stereoselective production of \(\gamma\)-oxyfunctionalyzed amino acids
- A stereoselective three-enzyme cascade for synthesis of diasteromerically pure \(\gamma\)-oxyfunctionalized \(\alpha\)-amino acids was developed. By coupling a dynamic kinetic resolution (DKR) using an \(\it N\)-acylamino acid racemase (NAAAR) and an L-selective aminoacylase from \(\textit {Geobacillus thermoglucosidasius}\) with a stereoselective isoleucine dioxygenase from \(\textit {Bacillus thuringiensis,}\) diastereomerically pure oxidized amino acids were produced from racemic \(\it N\)-acetylamino acids. The three enzymes differed in their optimal temperature and pH-spectra. Their different metal cofactor dependencies led to inhibitory effects. Under optimized conditions, racemic \(\it N\)-acetylmethionine was quantitatively converted into L-methionine-\(\textit {(S)}\)-sulfoxide with 97% yield and 95% \(\textit {de.}\) The combination of these three different biocatalysts allowed the direct synthesis of diastereopure oxyfunctionalized amino acids from inexpensive racemic starting material.
| Author: | Junichi EnokiGND, Jaqueline MeisbornGND, Ann-Christin MüllerGND, Robert KouristORCiDGND |
|---|---|
| URN: | urn:nbn:de:hbz:294-70019 |
| DOI: | https://doi.org/10.3389/fmicb.2016.00425 |
| Parent Title (English): | Frontiers in microbiology |
| Publisher: | Frontiers Media |
| Place of publication: | Lausanne |
| Document Type: | Article |
| Language: | English |
| Date of Publication (online): | 2020/02/17 |
| Date of first Publication: | 2016/04/07 |
| Publishing Institution: | Ruhr-Universität Bochum, Universitätsbibliothek |
| Tag: | amino acids; asymmetric oxidation; dynamic kinetic resolution; enzyme reaction; isoleucine dioxygenase; multi-enzyme cascade reaction |
| Volume: | 7 |
| First Page: | 425-1 |
| Last Page: | 425-8 |
| Institutes/Facilities: | Lehrstuhl für Pflanzenphysiologie, Nachwuchsgruppe Mikrobielle Biotechnologie |
| Research Department Interfacial Systems Chemistry | |
| open_access (DINI-Set): | open_access |
| faculties: | Fakultät für Biologie und Biotechnologie |
| Licence (English): |  Creative Commons - CC BY 4.0 - Attribution 4.0 International |
