ArticleChemical science2017
Sonogashira diversification of unprotected halotryptophans, halotryptophan containing tripeptides; and generation of a new to nature bromo-natural product and its diversification in water.
Article in Chemical science, 2017. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 21 papers.
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Who cites it
21 citing papers in PubMed, 44 citations in OpenAlex.
- Late-Stage Modification of Halotryptophan-Containing Peptides Via Negishi Cross-Coupling.Chemistry (Weinheim an der Bergstrasse, Germany) · 2026Article
- Synthesis of Amines for Active Pharmaceutical Ingredients Using the Whole-Cell Factory Saccharomyces Cerevisae.Chembiochem : a European journal of chemical biology · 2026Review
- Synthetic Biology in Natural Product Biosynthesis.Chemical reviews · 2025Review
- Halogenase-Assisted Alkyne/Aryl Bromide Sonogashira Coupling for Ribosomally Synthesized Peptides.Journal of the American Chemical Society · 2024Article
- Multiplexed Assessment of Promiscuous Non-Canonical Amino Acid Synthase Activity in a Pyridoxal Phosphate-Dependent Protein Family.ACS catalysis · 2023Article
- Halogenation of Peptides and Proteins Using Engineered Tryptophan Halogenase Enzymes.Biomolecules · 2022Article
- Opportunities for Expanding Encoded Chemical Diversification and Improving Hit Enrichment in mRNA-Displayed Peptide Libraries.Chembiochem : a European journal of chemical biology · 2022Review
- Site-Selective Cross-Coupling of Polyhalogenated Arenes and Heteroarenes with Identical Halogen Groups.Chemical reviews · 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
- Deploying Microbial Synthesis for Halogenating and Diversifying Medicinal Alkaloid Scaffolds.Frontiers in bioengineering and biotechnology · 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
- Facile in Vitro Biocatalytic Production of Diverse Tryptamines.Chembiochem : a European journal of chemical biology · 2019Article
- Bromination of L-tryptophan in a Fermentative Process WithFrontiers in bioengineering and biotechnology · 2019Article
- Biocatalytic Oxidation Reactions: A Chemist's Perspective.Angewandte Chemie (International ed. in English) · 2018Review
Corrections and comments
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Authors and funding
9 authors at 4 institutions in 5 countries.
Funding
Abstract
The blending together of synthetic chemistry with natural product biosynthesis represents a potentially powerful approach to synthesis; to enable this, further synthetic tools and methodologies are needed. To this end, we have explored the first Sonogashira cross-coupling to halotryptophans in water. Broad reaction scope is demonstrated and we have explored the limits of the scope of the reaction. We have demonstrated this methodology to work excellently in the modification of model tripeptides. Furthermore, through precursor directed biosynthesis, we have generated for the first time a new to nature brominated natural product bromo-cystargamide, and demonstrated the applicability of our reaction conditions to modify this novel metabolite.
Identifiers
What OpenQuestion holds
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.