Details
| Originalsprache | Englisch |
|---|---|
| Seiten (von - bis) | 7222-7228 |
| Seitenumfang | 7 |
| Fachzeitschrift | TETRAHEDRON |
| Jahrgang | 72 |
| Ausgabenummer | 46 |
| Frühes Online-Datum | 28 Nov. 2015 |
| Publikationsstatus | Veröffentlicht - 17 Nov. 2016 |
| Extern publiziert | Ja |
Abstract
A two-step Design of Experiments (DoE) strategy followed by a two-liquid-phase system (2LPS) was applied to enhance the ɛ-caprolactone yield in the cyclohexanone monooxygenase (CHMO)-alcohol dehydrogenase (ADH) convergent cascade system. The key reaction parameters were identified and optimized for the determination of an optimal operational window for the aqueous media. In the 2LPS system, high partitioning of the lactone product was observed in 2-MeTHF and in toluene; however, these solvents led to drastically reduced enzymatic activity. Dodecane was chosen as the non-miscible organic phase owing to the enzymes’ high residual activity, despite the low partitioning of the lactone. Cyclohexanone concentrations up to 75 mM were applied in the aqueous media. The turnover numbers for the nicotinamide cofactor and for the ADH reached up to 980 and 392,000, respectively whereas a turnover number value of 5600 was achieved for the CHMO. By employing a 2LPS, whereby 91 mM of cyclohexanone was applied in the second phase, turnover numbers were slightly increased.
ASJC Scopus Sachgebiete
- Biochemie, Genetik und Molekularbiologie (insg.)
- Biochemie
- Pharmakologie, Toxikologie und Pharmazie (insg.)
- Wirkstoffforschung
- Chemie (insg.)
- Organische Chemie
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in: TETRAHEDRON, Jahrgang 72, Nr. 46, 17.11.2016, S. 7222-7228.
Publikation: Beitrag in Fachzeitschrift › Artikel › Forschung › Peer-Review
}
TY - JOUR
T1 - Enhancing the productivity of the bi-enzymatic convergent cascade for ɛ-caprolactone synthesis through design of experiments and a biphasic system
AU - Bornadel, Amin
AU - Hatti-Kaul, Rajni
AU - Hollmann, Frank
AU - Kara, Selin
N1 - Funding Information: S.K. thanks DECHEMA e.V. (Frankfurt am Main, Germany) for financial support in the form of a ‘Max Buchner’ fellowship (Code 3412). R.H.K. thanks to Swedish Research Council (Vetenskapsrådet, Stockholm, Sweden) for the financial support. We gratefully acknowledge Dr. Caroline Paul (Delft University of Technology, The Netherlands) for proofreading the manuscript. The authors would like to thank Prof. Dr. Wolfgang Kroutil (University of Graz, Austria) for the plasmid hosting alcohol dehydrogenase from Thermoanaerobacter ethanolicus (TeSADH) and Prof. Dr. Marco W. Fraaije (University of Groningen, The Netherlands) for the plasmid hosting wild-type cyclohexanone monooxygenase (CHMO) from Acinetobacter sp. NCIMB 9871 (CRE2-CHMO).
PY - 2016/11/17
Y1 - 2016/11/17
N2 - A two-step Design of Experiments (DoE) strategy followed by a two-liquid-phase system (2LPS) was applied to enhance the ɛ-caprolactone yield in the cyclohexanone monooxygenase (CHMO)-alcohol dehydrogenase (ADH) convergent cascade system. The key reaction parameters were identified and optimized for the determination of an optimal operational window for the aqueous media. In the 2LPS system, high partitioning of the lactone product was observed in 2-MeTHF and in toluene; however, these solvents led to drastically reduced enzymatic activity. Dodecane was chosen as the non-miscible organic phase owing to the enzymes’ high residual activity, despite the low partitioning of the lactone. Cyclohexanone concentrations up to 75 mM were applied in the aqueous media. The turnover numbers for the nicotinamide cofactor and for the ADH reached up to 980 and 392,000, respectively whereas a turnover number value of 5600 was achieved for the CHMO. By employing a 2LPS, whereby 91 mM of cyclohexanone was applied in the second phase, turnover numbers were slightly increased.
AB - A two-step Design of Experiments (DoE) strategy followed by a two-liquid-phase system (2LPS) was applied to enhance the ɛ-caprolactone yield in the cyclohexanone monooxygenase (CHMO)-alcohol dehydrogenase (ADH) convergent cascade system. The key reaction parameters were identified and optimized for the determination of an optimal operational window for the aqueous media. In the 2LPS system, high partitioning of the lactone product was observed in 2-MeTHF and in toluene; however, these solvents led to drastically reduced enzymatic activity. Dodecane was chosen as the non-miscible organic phase owing to the enzymes’ high residual activity, despite the low partitioning of the lactone. Cyclohexanone concentrations up to 75 mM were applied in the aqueous media. The turnover numbers for the nicotinamide cofactor and for the ADH reached up to 980 and 392,000, respectively whereas a turnover number value of 5600 was achieved for the CHMO. By employing a 2LPS, whereby 91 mM of cyclohexanone was applied in the second phase, turnover numbers were slightly increased.
KW - Caprolactone
KW - Design of experiments
KW - Enzymatic cascades
KW - Oxidoreductases
KW - Two-liquid-phase system
UR - http://www.scopus.com/inward/record.url?scp=84950123144&partnerID=8YFLogxK
U2 - 10.1016/j.tet.2015.11.054
DO - 10.1016/j.tet.2015.11.054
M3 - Article
AN - SCOPUS:84950123144
VL - 72
SP - 7222
EP - 7228
JO - TETRAHEDRON
JF - TETRAHEDRON
SN - 0040-4020
IS - 46
ER -