Academic Journal
Optimized enantioselective (S)-2-hydroxypropiophenone synthesis by free- and encapsulated-resting cells of Pseudomonas putida
| العنوان: | Optimized enantioselective (S)-2-hydroxypropiophenone synthesis by free- and encapsulated-resting cells of Pseudomonas putida |
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| المؤلفون: | Reihaneh Kordesedehi, Mohammad Ali Asadollahi, Azar Shahpiri, Davoud Biria, Pablo Iván Nikel |
| المصدر: | Microbial Cell Factories, Vol 22, Iss 1, Pp 1-11 (2023) |
| بيانات النشر: | BMC |
| سنة النشر: | 2023 |
| المجموعة: | Directory of Open Access Journals: DOAJ Articles |
| مصطلحات موضوعية: | αHydroxyketones, 2-Hydroxypropiophenone, Pseudomonas putida, Benzoylformate decarboxylase (BFD), Cell immobilization, Biotransformation, Microbiology, QR1-502 |
| الوصف: | Background Aromatic α-hydroxy ketones, such as S-2-hydroxypropiophenone (2-HPP), are highly valuable chiral building blocks useful for the synthesis of various pharmaceuticals and natural products. In the present study, enantioselective synthesis of 2-HPP was investigated by free and immobilized whole cells of Pseudomonas putida ATCC 12633 starting from readily-available aldehyde substrates. Whole resting cells of P. putida, previously grown in a culture medium containing ammonium mandelate, are a source of native benzoylformate decarboxylase (BFD) activity. BFD produced by induced P. putida resting cells is a highly active biocatalyst without any further treatment in comparison with partially purified enzyme preparations. These cells can convert benzaldehyde and acetaldehyde into the acyloin compound 2-HPP by BFD-catalyzed enantioselective cross-coupling reaction. Results The reaction was carried out in the presence of exogenous benzaldehyde (20 mM) and acetaldehyde (600 mM) as substrates in 6 mL of 200 mM phosphate buffer (pH 7) for 3 h. The optimal biomass concentration was assessed to be 0.006 g dry cell weight (DCW) mL− 1. 2-HPP titer, yield and productivity using the free cells were 1.2 g L− 1, 0.56 g 2-HPP/g benzaldehyde (0.4 mol 2-HPP/mol benzaldehyde), 0.067 g 2-HPP g− 1 DCW h− 1, respectively, under optimized biotransformation conditions (30 °C, 200 rpm). Calcium alginate (CA)–polyvinyl alcohol (PVA)-boric acid (BA)-beads were used for cell entrapment. Encapsulated whole-cells were successfully employed in four consecutive cycles for 2-HPP production under aerobic conditions without any noticeable beads degradation. Moreover, there was no production of benzyl alcohol as an unwanted by-product. Conclusions Bioconversion by whole P. putida resting cells is an efficient strategy for the production of 2-HPP and other α-hydroxyketones. Graphical abstract |
| نوع الوثيقة: | article in journal/newspaper |
| اللغة: | English |
| تدمد: | 1475-2859 |
| Relation: | https://doi.org/10.1186/s12934-023-02073-7; https://doaj.org/toc/1475-2859; https://doaj.org/article/959387974e9c4ce0b38d18e8f747eeb9 |
| DOI: | 10.1186/s12934-023-02073-7 |
| الاتاحة: | https://doi.org/10.1186/s12934-023-02073-7 https://doaj.org/article/959387974e9c4ce0b38d18e8f747eeb9 |
| رقم الانضمام: | edsbas.2584ED6B |
| قاعدة البيانات: | BASE |
Full Text Finder | تدمد: | 14752859 |
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| DOI: | 10.1186/s12934-023-02073-7 |