Details
| Original language | English |
|---|---|
| Pages (from-to) | 2418-2426 |
| Number of pages | 9 |
| Journal | Catalysis Science and Technology |
| Volume | 5 |
| Issue number | 4 |
| Early online date | 3 Feb 2015 |
| Publication status | Published - 1 Apr 2015 |
| Externally published | Yes |
Abstract
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. This journal is
ASJC Scopus subject areas
- Chemical Engineering(all)
- Catalysis
Cite this
- Standard
- Harvard
- Apa
- Vancouver
- BibTeX
- RIS
In: Catalysis Science and Technology, Vol. 5, No. 4, 01.04.2015, p. 2418-2426.
Research output: Contribution to journal › Article › Research › peer review
}
TY - JOUR
T1 - Reversibility of asymmetric catalyzed C-C bond formation by benzoylformate decarboxylase
AU - Berheide, Marco
AU - Kara, Selin
AU - Liese, Andreas
PY - 2015/4/1
Y1 - 2015/4/1
N2 - 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. This journal is
AB - 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. This journal is
UR - http://www.scopus.com/inward/record.url?scp=84925855386&partnerID=8YFLogxK
U2 - 10.1039/c4cy00171k
DO - 10.1039/c4cy00171k
M3 - Article
AN - SCOPUS:84925855386
VL - 5
SP - 2418
EP - 2426
JO - Catalysis Science and Technology
JF - Catalysis Science and Technology
SN - 2044-4753
IS - 4
ER -