Enzymatic Halogenation of Tryptophan on a Gram Scale

Frese M, Sewald N (2015)
Angewandte Chemie International Edition 54(1): 298-301.

Zeitschriftenaufsatz | Veröffentlicht | Englisch
 
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Abstract / Bemerkung
Halogenated arenes are important building blocks in medicinal and agrochemistry. Chemical electrophilic aromatic halogenation requires molecular halogen, whereas FAD-dependent halogenases form halogenated arenes with high regioselectivity while only halide salts and O-2 are required. This reaction proceeds at room temperature in aqueous media. However, enzymatic halogenation is considered inefficient, mainly because halogenases are not stable. Thus, the preparative application remained elusive. We were able to show that the long-term stability and, hence, the preparative efficiency of the tryptophan-7-halogenase RebH can be significantly improved by immobilization together with the other enzymes required for cofactor regeneration. We established a facile scalable method suitable for the halogenation of tryptophan and its derivatives on a gram scale using a solid, multifunctional, and recyclable biocatalyst; this immobilization strategy might also be applicable for other FAD-dependent halogenases.
Stichworte
sustainable chemistry; regioselectivity; halogenases; biocatalysis; enzyme immobilization
Erscheinungsjahr
2015
Zeitschriftentitel
Angewandte Chemie International Edition
Band
54
Ausgabe
1
Seite(n)
298-301
ISSN
1433-7851
Page URI
https://pub.uni-bielefeld.de/record/2719020

Zitieren

Frese M, Sewald N. Enzymatic Halogenation of Tryptophan on a Gram Scale. Angewandte Chemie International Edition. 2015;54(1):298-301.
Frese, M., & Sewald, N. (2015). Enzymatic Halogenation of Tryptophan on a Gram Scale. Angewandte Chemie International Edition, 54(1), 298-301. doi:10.1002/anie.201408561
Frese, M., and Sewald, N. (2015). Enzymatic Halogenation of Tryptophan on a Gram Scale. Angewandte Chemie International Edition 54, 298-301.
Frese, M., & Sewald, N., 2015. Enzymatic Halogenation of Tryptophan on a Gram Scale. Angewandte Chemie International Edition, 54(1), p 298-301.
M. Frese and N. Sewald, “Enzymatic Halogenation of Tryptophan on a Gram Scale”, Angewandte Chemie International Edition, vol. 54, 2015, pp. 298-301.
Frese, M., Sewald, N.: Enzymatic Halogenation of Tryptophan on a Gram Scale. Angewandte Chemie International Edition. 54, 298-301 (2015).
Frese, Marcel, and Sewald, Norbert. “Enzymatic Halogenation of Tryptophan on a Gram Scale”. Angewandte Chemie International Edition 54.1 (2015): 298-301.

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