Advanced

Enhancing the productivity of the bi-enzymatic convergent cascade for ɛ-caprolactone synthesis through design of experiments and a biphasic system

Bornadel, Amin LU ; Hatti-Kaul, Rajni LU ; Hollmann, Frank and Kara, Selin (2016) In Tetrahedron 72(46). p.7222-7228
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... (More)

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.

(Less)
Please use this url to cite or link to this publication:
author
organization
publishing date
type
Contribution to journal
publication status
published
subject
keywords
Caprolactone, Design of experiments, Enzymatic cascades, Oxidoreductases, Two-liquid-phase system
in
Tetrahedron
volume
72
issue
46
pages
7 pages
publisher
Elsevier
external identifiers
  • scopus:84950123144
  • wos:000386861000005
ISSN
0040-4020
DOI
10.1016/j.tet.2015.11.054
language
English
LU publication?
yes
id
af189a64-4db8-40e8-bc2a-11be3c7955a3
date added to LUP
2016-11-04 10:30:41
date last changed
2017-10-22 05:21:29
@article{af189a64-4db8-40e8-bc2a-11be3c7955a3,
  abstract     = {<p>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.</p>},
  author       = {Bornadel, Amin and Hatti-Kaul, Rajni and Hollmann, Frank and Kara, Selin},
  issn         = {0040-4020},
  keyword      = {Caprolactone,Design of experiments,Enzymatic cascades,Oxidoreductases,Two-liquid-phase system},
  language     = {eng},
  month        = {11},
  number       = {46},
  pages        = {7222--7228},
  publisher    = {Elsevier},
  series       = {Tetrahedron},
  title        = {Enhancing the productivity of the bi-enzymatic convergent cascade for ɛ-caprolactone synthesis through design of experiments and a biphasic system},
  url          = {http://dx.doi.org/10.1016/j.tet.2015.11.054},
  volume       = {72},
  year         = {2016},
}