Novel Arylindigoids by Late-Stage Derivatization of Biocatalytically Synthesized Dibromoindigo
© 2021 The Authors. Published by Wiley-VCH GmbH..
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.
Medienart: |
E-Artikel |
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Erscheinungsjahr: |
2021 |
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Erschienen: |
2021 |
Enthalten in: |
Zur Gesamtaufnahme - volume:27 |
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Enthalten in: |
Chemistry (Weinheim an der Bergstrasse, Germany) - 27(2021), 17 vom: 22. März, Seite 5404-5411 |
Sprache: |
Englisch |
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Beteiligte Personen: |
Schnepel, Christian [VerfasserIn] |
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Links: |
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Themen: |
8DUH1N11BX |
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Anmerkungen: |
Date Completed 24.03.2021 Date Revised 11.11.2023 published: Print-Electronic Citation Status MEDLINE |
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doi: |
10.1002/chem.202005191 |
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funding: |
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PPN (Katalog-ID): |
NLM320583511 |
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520 | |a 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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