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Catalytic Scope of the Thiamine-Dependent Multifunctional Enzyme Cyclohexane-1,2-dione Hydrolase

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2014

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Loschonsky, Sabrina
Waltzer, Simon
Fraas, Sonja
Wacker, Tobias
Andrade, Susana L. A.

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https://doi.org/10.1002/cbic.201300673
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ChemBioChem. 2014, 15(3), pp. 389-392. ISSN 1439-4227. eISSN 1439-7633. Available under: doi: 10.1002/cbic.201300673

Zusammenfassung

The thiamine diphosphate (ThDP)-dependent enzyme cyclohexane-1,2-dione hydrolase (CDH) was expressed in Escherichia coli and purified by affinity chromatography (Ni-NTA). Recombinant CDH showed the same C-C bond-cleavage and C-C bond-formation activities as the native enzyme. Furthermore, we have shown that CDH catalyzes the asymmetric cross-benzoin reaction of aromatic aldehydes and (decarboxylated) pyruvate (up to quantitative conversion, 92–99 % ee). CDH accepts also hydroxybenzaldehydes and nitrobenzaldehydes; these previously have not (or only in rare cases) been known as substrates of other ThDP-dependent enzymes. On a semipreparative scale, sterically demanding 4-(tert-butyl)benzaldehyde and 2-naphthaldehyde were transformed into the corresponding 2-hydroxy ketone products in high yields. Additionally, certain benzaldehydes with electron withdrawing substituents were identified as potential inhibitors of the ligase activity of CDH.

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570 Biowissenschaften, Biologie

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asymmetric catalysis, C-C bond-formation, carboligation, enzyme catalysis, ThDP

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ISO 690LOSCHONSKY, Sabrina, Simon WALTZER, Sonja FRAAS, Tobias WACKER, Susana L. A. ANDRADE, Peter M. H. KRONECK, Michael MÜLLER, 2014. Catalytic Scope of the Thiamine-Dependent Multifunctional Enzyme Cyclohexane-1,2-dione Hydrolase. In: ChemBioChem. 2014, 15(3), pp. 389-392. ISSN 1439-4227. eISSN 1439-7633. Available under: doi: 10.1002/cbic.201300673
BibTex
@article{Loschonsky2014Catal-30066,
  year={2014},
  doi={10.1002/cbic.201300673},
  title={Catalytic Scope of the Thiamine-Dependent Multifunctional Enzyme Cyclohexane-1,2-dione Hydrolase},
  number={3},
  volume={15},
  issn={1439-4227},
  journal={ChemBioChem},
  pages={389--392},
  author={Loschonsky, Sabrina and Waltzer, Simon and Fraas, Sonja and Wacker, Tobias and Andrade, Susana L. A. and Kroneck, Peter M. H. and Müller, Michael}
}
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