2023
DOI: 10.1039/d2re00461e
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Halohydrin dehalogenase-catalysed synthesis of enantiopure fluorinated building blocks: bottlenecks found and explained by applying a reaction engineering approach

Abstract: Optically pure fluorinated organic azides represent synthetically valuable building blocks in a range of industrial applications. Since direct fluorination of molecules is challenging from both economic and environmental perspective, the...

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Cited by 6 publications
(10 citation statements)
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“…On the other hand, in the presence of higher rac -1 concentrations, the deactivation was more severe, whereby the highest deactivation rate was recorded at the highest epoxide concentration (Figure B). This data trend insinuates that epoxide amount could have an important role in enzyme operational stability as well. ,, Such behavior could be due to esterification of protein carboxyl groups or nonspecific chemical reactions between epoxide rings and protein functional groups of a nucleophilic character, such as amino-, hydroxyl-, or thiol- groups, leading to random alterations on the protein surface. , …”
Section: Resultsmentioning
confidence: 96%
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“…On the other hand, in the presence of higher rac -1 concentrations, the deactivation was more severe, whereby the highest deactivation rate was recorded at the highest epoxide concentration (Figure B). This data trend insinuates that epoxide amount could have an important role in enzyme operational stability as well. ,, Such behavior could be due to esterification of protein carboxyl groups or nonspecific chemical reactions between epoxide rings and protein functional groups of a nucleophilic character, such as amino-, hydroxyl-, or thiol- groups, leading to random alterations on the protein surface. , …”
Section: Resultsmentioning
confidence: 96%
“…For example, epoxides act as inhibitors in both biocatalytic reactions. Moreover, inhibitions by the opposite enantiomers of the substrate, the formed biocatalytic product, the byproduct diol, and the cosolvent DMSO are present as well, 35 whereby the latter was also confirmed in other investigated HHDH-catalyzed reactions. 34 In our first studies regarding HHDH-catalyzed transformations of fluorinated styrene oxide derivatives, we have found that cyanolysis reactions, despite representing a high potential for the synthesis of optically pure valuable compounds, proceed with reduced efficiency on a higher concentration scale.…”
Section: Resultsmentioning
confidence: 99%
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