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

Erscheinungsjahr:

2021

Erschienen:

2021

Enthalten in:

Zur Gesamtaufnahme - volume:27

Enthalten in:

Chemistry (Weinheim an der Bergstrasse, Germany) - 27(2021), 17 vom: 22. März, Seite 5404-5411

Sprache:

Englisch

Beteiligte Personen:

Schnepel, Christian [VerfasserIn]
Dodero, Veronica I [VerfasserIn]
Sewald, Norbert [VerfasserIn]

Links:

Volltext

Themen:

8DUH1N11BX
C−H functionalization
Cascade
Flavins
Halogenase
Halogens
Heterocycles
Journal Article
Monooxygenase
Tryptophan

Anmerkungen:

Date Completed 24.03.2021

Date Revised 11.11.2023

published: Print-Electronic

Citation Status MEDLINE

doi:

10.1002/chem.202005191

funding:

Förderinstitution / Projekttitel:

PPN (Katalog-ID):

NLM320583511