- AutorIn
- Dr. Selin Kara
- Dr. Marco Berheide
- Prof. Dr. Andreas Liese
- Titel
- Reversibility of asymmetric catalyzed C–C bond formation by benzoylformate decarboxylase
- Zitierfähige Url:
- https://nbn-resolving.org/urn:nbn:de:bsz:14-qucosa-189019
- Quellenangabe
- Catalysis Science & Technology, Vol. 5 (2015),S. 2418-2426, ISSN 2044-4753
- Erstveröffentlichung
- 2015
- Abstract (DE)
- Dieser Beitrag ist mit Zustimmung des Rechteinhabers aufgrund einer (DFG-geförderten) Allianz- bzw. Nationallizenz frei zugänglich.
- Abstract (EN)
- Benzoylformate decarboxylase (BFD) from Pseudomonas putida catalyzed the formation of 2-hydroxy-1-phenylpropanone (2-HPP), a 2-hydroxy ketone, from the kinetic resolution of rac-benzoin in the presence of acetaldehyde. The formation rate of 2-HPP via kinetic resolution of benzoin was 700-fold lower compared to the formation via direct carboligation of benzaldehyde and acetaldehyde. Further investigations revealed that BFD not only accepts (R)-benzoin but also 2-HPP as the substrate. A typical Michaelis–Menten type kinetics was observed starting from enantiopure (S)- or (R)-2-HPP. The formation of racemic 2-HPP while using benzoin as the donor in the presence of acetaldehyde and the racemization of (R/S)-2-HPP were detected. The equilibrium constant determined, showed favoured conditions towards the product side i.e. (R)-benzoin and 2-HPP. In the end, an extended reaction mechanism was proposed by supplementing the already known mechanism with the C–C bond cleavage activity of BFD towards 2-hydroxy ketones.
- Andere Ausgabe
- DOI: 10.1039/c4cy00171k
- Volltext des Artikels, der zuerst in der Zeitschrift 'Catalysis Science & Technology' des Royal Society of Chemistry-Verlages erschienen ist.
Link: http://dx.doi.org/10.1039/c4cy00171k - Freie Schlagwörter (DE)
- Biotechnologie, Molekular Biotechnologie
- Freie Schlagwörter (EN)
- Biotechnology, Molecular Biotechnology
- Verlag
- Royal Society of Chemistry, Cambridge
- URN Qucosa
- urn:nbn:de:bsz:14-qucosa-189019
- Veröffentlichungsdatum Qucosa
- 04.01.2016
- Dokumenttyp
- Artikel
- Sprache des Dokumentes
- Englisch
- Lizenz / Rechtehinweis
- CC BY 3.0 DE