2022
DOI: 10.1002/adsc.202200342
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Expanding the Scope of Enantioselective Halohydrin Dehalogenases – Group B

Abstract: Halohydrin dehalogenases (HHDHs) possess an unnatural activity of introducing functionalities such as N3, CN, NO2 etc., into a molecule through the ring‐opening reaction of epoxides. The enantioselectivity of HHDHs is substrate‐dependent and not always high enough for synthetic applications. B‐group of HHDHs has been neglected in the past, due to observed low enantioselectivity based on performance on a relatively limited number of substrates. Extensive screening of substrates on HheB2 from Mycobacterium sp. G… Show more

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Cited by 14 publications
(8 citation statements)
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“…A steric factor is probably not responsible for such behaviour, since the difference in size between F and H atoms is only ∼10%; for the unsubstituted SO, E > 200 was found in the reaction catalysed by HheC. 19 A possible explanation is that the differences in the positions of F atoms, and thus different charge distributions, could affect the orientation of the ligand and the activation energy, 28 and consequently enantiodiscrimination. Accordingly, the presence of ortho -F significantly reduces the enantioselectivity of ortho , para -disubstituted derivatives 1h and 1j to E = 17 and E = 36, respectively (Table 2, entries 8 and 10).…”
Section: Resultsmentioning
confidence: 99%
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“…A steric factor is probably not responsible for such behaviour, since the difference in size between F and H atoms is only ∼10%; for the unsubstituted SO, E > 200 was found in the reaction catalysed by HheC. 19 A possible explanation is that the differences in the positions of F atoms, and thus different charge distributions, could affect the orientation of the ligand and the activation energy, 28 and consequently enantiodiscrimination. Accordingly, the presence of ortho -F significantly reduces the enantioselectivity of ortho , para -disubstituted derivatives 1h and 1j to E = 17 and E = 36, respectively (Table 2, entries 8 and 10).…”
Section: Resultsmentioning
confidence: 99%
“…Thus, the kinetic and thermodynamic parameters of the reaction can be expected to be different in HheC-M4 compared to HheC. 28…”
Section: Resultsmentioning
confidence: 99%
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“…Thermal corrections were extracted from the corresponding frequency calculations so that all presented results correspond to Gibbs free energies at room temperature and normal pressure. The choice of such computational setup was prompted by its success in reproducing various features of different organic, 30,31 organometallic, 32 and protein systems, [33][34][35] being particularly accurate for relative trends among similar systems, which is the focus here. In addition, the validity of the SMD implicit model in evaluating solvation effects on the reactivity parameters has recently been emphasized by various groups.…”
Section: Computational Detailsmentioning
confidence: 99%