Novel Arylindigoids by Late-Stage Derivatization of Biocatalytically Synthesized Dibromoindigo.

Schnepel C, Dodero VI, Sewald N (2021)
Chemistry - A European Journal 27(17): 5404-5411.

Zeitschriftenaufsatz | Veröffentlicht | Englisch
 
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Abstract / Bemerkung
Indigoids represent natural product-based compounds applicable as organic semiconductors and photoresponsive materials. Yet modified indigo derivatives are difficult to access by chemical synthesis. Thus a biocatalytic approach applying several consecutive selective C-H functionalizations was developed that selectively provides access to various indigoids: Enzymatic halogenation of l-tryptophan followed by indole generation with tryptophanase yields 5-, 6- and 7-bromoindoles. Subsequent hydroxylation using a flavin monooxygenase furnishes dibromoindigo that is derivatized by acylation. This four-step one-pot cascade gives Boc-protected dibromoindigo in good isolated yields. The halogen substituent allows for late-stage diversification by cross-coupling directly performed in the crude mixture, thus enabling synthesis of 5,5'- and 6,6'-diarylindigo derivatives. This chemoenzymatic approach provides a modular platform towards novel indigoids with attractive spectral properties. © 2021 Wiley-VCH GmbH.
Erscheinungsjahr
2021
Zeitschriftentitel
Chemistry - A European Journal
Band
27
Ausgabe
17
Seite(n)
5404-5411
eISSN
1521-3765
Finanzierungs-Informationen
Open-Access-Publikationskosten wurden durch die Universität Bielefeld im Rahmen des DEAL-Vertrags gefördert.
Page URI
https://pub.uni-bielefeld.de/record/2951152

Zitieren

Schnepel C, Dodero VI, Sewald N. Novel Arylindigoids by Late-Stage Derivatization of Biocatalytically Synthesized Dibromoindigo. Chemistry - A European Journal . 2021;27(17):5404-5411.
Schnepel, C., Dodero, V. I., & Sewald, N. (2021). Novel Arylindigoids by Late-Stage Derivatization of Biocatalytically Synthesized Dibromoindigo. Chemistry - A European Journal , 27(17), 5404-5411. https://doi.org/10.1002/chem.202005191
Schnepel, C., Dodero, V. I., and Sewald, N. (2021). Novel Arylindigoids by Late-Stage Derivatization of Biocatalytically Synthesized Dibromoindigo. Chemistry - A European Journal 27, 5404-5411.
Schnepel, C., Dodero, V.I., & Sewald, N., 2021. Novel Arylindigoids by Late-Stage Derivatization of Biocatalytically Synthesized Dibromoindigo. Chemistry - A European Journal , 27(17), p 5404-5411.
C. Schnepel, V.I. Dodero, and N. Sewald, “Novel Arylindigoids by Late-Stage Derivatization of Biocatalytically Synthesized Dibromoindigo.”, Chemistry - A European Journal , vol. 27, 2021, pp. 5404-5411.
Schnepel, C., Dodero, V.I., Sewald, N.: Novel Arylindigoids by Late-Stage Derivatization of Biocatalytically Synthesized Dibromoindigo. Chemistry - A European Journal . 27, 5404-5411 (2021).
Schnepel, Christian, Dodero, Veronica Isabel, and Sewald, Norbert. “Novel Arylindigoids by Late-Stage Derivatization of Biocatalytically Synthesized Dibromoindigo.”. Chemistry - A European Journal 27.17 (2021): 5404-5411.
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2021-03-23T09:59:32Z
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