ArticleChemistry (Weinheim an der Bergstrasse, Germany)2019
Heck Diversification of Indole-Based Substrates under Aqueous Conditions: From Indoles to Unprotected Halo-tryptophans and Halo-tryptophans in Natural Product Derivatives.
Article in Chemistry (Weinheim an der Bergstrasse, Germany), 2019. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 17 papers.
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Who cites it
17 citing papers in PubMed, 21 citations in OpenAlex.
- Late-Stage Modification of Halotryptophan-Containing Peptides Via Negishi Cross-Coupling.Chemistry (Weinheim an der Bergstrasse, Germany) · 2026Article
- Barettin Suppresses Pancreatic Ductal Adenocarcinoma Proliferation via Topoisomerase IIα Inhibition.Marine drugs · 2026Article
- Arylation of Olefins with N-Unprotected Bromobisindole Ethanamines: Expanding the Scope of the Mizoroki-Heck Reaction.The Journal of organic chemistry · 2026Article
- Barettin, a Nonopioid, Nonhallucinogenic Marine Natural Product with Antihyperalgesic Properties Mediated by 5HT2A Inverse Agonism.Journal of natural products · 2026Article
- Regioselective C─H Functionalization by the Combination of Enzymatic and Chemocatalytic Reactions in Water.Angewandte Chemie (International ed. in English) · 2025Article
- Efficient and Rapid Arylation of NH₂-Unprotected Bromobisindole Ethanamines via Suzuki-Miyaura Coupling: Generating New Leads Against Leishmania.Chemistry (Weinheim an der Bergstrasse, Germany) · 2025Article
- Synthetic Biology in Natural Product Biosynthesis.Chemical reviews · 2025Review
- Effects of Structurally Different HDAC Inhibitors againstACS infectious diseases · 2022Article
- Opportunities for Expanding Encoded Chemical Diversification and Improving Hit Enrichment in mRNA-Displayed Peptide Libraries.Chembiochem : a European journal of chemical biology · 2022Review
- Peptide stapling by late-stage Suzuki-Miyaura cross-coupling.Beilstein journal of organic chemistry · 2022Article
- Negishi Cross-Coupling Provides Alkylated Tryptophans and Tryptophan Regioisomers.Chemistry (Weinheim an der Bergstrasse, Germany) · 2021Article
- An expedient, mild and aqueous method for Suzuki-Miyaura diversification of (hetero)aryl halides or (poly)chlorinated pharmaceuticals.Organic chemistry frontiers : an international journal of organic chemistry · 2021Article
- Halogenases: a palette of emerging opportunities for synthetic biology-synthetic chemistry and C-H functionalisation.Chemical Society reviews · 2021Review
- Enzymkatalysierte späte Modifizierungen: Besser spät als nie.Angewandte Chemie (Weinheim an der Bergstrasse, Germany) · 2021Review
- Enzymatic Late-Stage Modifications: Better Late Than Never.Angewandte Chemie (International ed. in English) · 2021Review
- Late-Stage Diversification of Tryptophan-Derived Biomolecules.Chemistry (Weinheim an der Bergstrasse, Germany) · 2020Review
- Heck Diversification of Indole-Based Substrates under Aqueous Conditions: From Indoles to Unprotected Halo-tryptophans and Halo-tryptophans in Natural Product Derivatives.Chemistry (Weinheim an der Bergstrasse, Germany) · 2019Article
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Authors and funding
6 authors at 3 institutions in 2 countries.
Funding
Abstract
The blending of synthetic chemistry with biosynthetic processes provides a powerful approach to synthesis. Biosynthetic halogenation and synthetic cross-coupling have great potential to be used together, for small molecule generation, access to natural product analogues and as a tool for chemical biology. However, to enable enhanced generality of this approach, further synthetic tools are needed. Though considerable research has been invested in the diversification of phenylalanine and tyrosine, functionalisation of tryptophans thorough cross-coupling has been largely neglected. Tryptophan is a key residue in many biologically active natural products and peptides; in proteins it is key to fluorescence and dominates protein folding. To this end, we have explored the Heck cross-coupling of halo-indoles and halo-tryptophans in water, showing broad reaction scope. We have demonstrated the ability to use this methodology in the functionalisation of a brominated antibiotic (bromo-pacidamycin), as well as a marine sponge metabolite, barettin.
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Registered trials
Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.