10.1021/acs.oprd.8b00079.s001
Marie
A. F. Delgove
Marie
A. F.
Delgove
Matthew T. Elford
Matthew T.
Elford
Katrien V. Bernaerts
Katrien V.
Bernaerts
Stefaan M. A. De Wildeman
Stefaan M. A. De
Wildeman
Toward Upscaled Biocatalytic Preparation of Lactone
Building Blocks for Polymer Applications
American Chemical Society
2018
Upscaled Biocatalytic Preparation
substrate
product concentration
thermostable cyclohexanone monooxygenase
lactone
CSF
BVMO
Lactone Building Blocks
strategy
synthesis
GDH
application
2018-06-12 00:00:00
Journal contribution
https://acs.figshare.com/articles/journal_contribution/Toward_Upscaled_Biocatalytic_Preparation_of_Lactone_Building_Blocks_for_Polymer_Applications/6634382
Although
Baeyer–Villiger monooxygenases (BVMOs) have gained
attention in recent years, there are few cases of their upscaled application
for lactone synthesis. A thermostable cyclohexanone monooxygenase
from Thermocrispum municipale (TmCHMO)
was applied to the oxidation of 3,3,5-trimethylcyclohexanone using
a glucose dehydrogenase (GDH) for cofactor regeneration. The reaction
progress was improved by optimizing the biocatalyst loading, with
investigation into oxygen limitations. The product concentration and
productivity were increased by keeping the substrate concentration
below the inhibitory level via continuous substrate feeding (CSF).
This substrate feeding strategy was evaluated against two biphasic
reactions using either toluene or <i>n</i>-butyl acetate
as immiscible organic solvents. A product concentration of 38 g L<sup>–1</sup> and a space-time yield of 1.35 g L<sup>–1</sup> h<sup>–1</sup> were achieved during the gram-scale synthesis
of the two regioisomeric lactones by applying the CSF strategy. These
improvements contribute to the large-scale application of BVMOs in
the synthesis of branched building blocks for polymer applications.