ArticleChemistry (Weinheim an der Bergstrasse, Germany)2021
Novel Arylindigoids by Late-Stage Derivatization of Biocatalytically Synthesized Dibromoindigo.
Article in Chemistry (Weinheim an der Bergstrasse, Germany), 2021. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 6 papers.
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Who cites it
6 citing papers in PubMed.
- Engineering artificial biosynthetic pathway enables simultaneous production and in-situ bio-dyeing of indigoids for textiles.Nature communications · 2025Article
- Enzymatic Late-Stage Halogenation of Peptides.Chembiochem : a European journal of chemical biology · 2023Article
- Oxygenating Biocatalysts for Hydroxyl Functionalisation in Drug Discovery and Development.ChemMedChem · 2022Review
- Peptide stapling by late-stage Suzuki-Miyaura cross-coupling.Beilstein journal of organic chemistry · 2022Article
- Identification of an indole biodegradation gene cluster fromFrontiers in bioengineering and biotechnology · 2022Article
- Novel Arylindigoids by Late-Stage Derivatization of Biocatalytically Synthesized Dibromoindigo.Chemistry (Weinheim an der Bergstrasse, Germany) · 2021Article
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Abstract
Indigoids represent natural product-based compounds applicable as organic semiconductors and photoresponsive materials. Yet modified indigo derivatives are difficult to access by chemical synthesis. 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 dibromoindigo in good isolated yields. Moreover, the halogen substituent allows for late-stage diversification by cross-coupling directly performed in the crude mixture, thus enabling synthesis of a small set of 6,6'-diarylindigo derivatives. This chemoenzymatic approach provides a modular platform towards novel indigoids with attractive spectral properties.
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