ArticleChembiochem : a European journal of chemical biology2020
Direct Enzymatic Synthesis of a Deep-Blue Fluorescent Noncanonical Amino Acid from Azulene and Serine.
Article in Chembiochem : a European journal of chemical biology, 2020. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 16 papers.
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Who cites it
16 citing papers in PubMed, 34 citations in OpenAlex.
- Detecting Vibrational Energy Transfer into an Enzyme Active Site via a Transition State Analog.The journal of physical chemistry letters · 2026Article
- A novel cyan-emitting fluorescent α-amino acid: synthesis, photophysical characterization and live-cell imaging properties.RSC advances · 2026Article
- Synthesis of l-β-(6-azulenyl)alanine and the fluorescent actin disruptor (6-azuleno)chalasin H.RSC advances · 2025Article
- α-Hydrazino Acids Inhibit Pyridoxal Phosphate-Dependent Decarboxylases via "Catalytically Correct" Ketoenamine Tautomers: A Special Motif for Chemical Biology and Drug Discovery?ACS catalysis · 2025Article
- Exploiting Archaeal/Thermostable Enzymes in Synthetic Chemistry: Back to the Future?ChemCatChem · 2024Article
- The β-subunit of tryptophan synthase is a latent tyrosine synthase.Nature chemical biology · 2024Article
- Engineered Biocatalytic Synthesis of β-N-Substituted-α-Amino Acids.Angewandte Chemie (International ed. in English) · 2023Article
- Biocatalytic Friedel-Crafts Reactions.ChemCatChem · 2022Review
- Versatile Vibrational Energy Sensors for Proteins.Angewandte Chemie (International ed. in English) · 2022Article
- Asymmetric Alkylation of Ketones Catalyzed by Engineered TrpB.Angewandte Chemie (International ed. in English) · 2021Article
- Through bonds or contacts? Mapping protein vibrational energy transfer using non-canonical amino acids.Nature communications · 2021Article
- Azulene-A Bright Core for Sensing and Imaging.Molecules (Basel, Switzerland) · 2021Review
- Tryptophan Synthase: Biocatalyst Extraordinaire.Chembiochem : a European journal of chemical biology · 2021Review
- Scalable continuous evolution for the generation of diverse enzyme variants encompassing promiscuous activities.Nature communications · 2020Article
- Facile synthesis of a novel genetically encodable fluorescent α-amino acid emitting greenish blue light.Chemical communications (Cambridge, England) · 2020Article
- Overview on Multienzymatic Cascades for the Production of Non-canonical α-Amino Acids.Frontiers in bioengineering and biotechnology · 2020Review
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Authors and funding
3 authors at 1 institution in 1 country.
Funding
Abstract
We report a simple, one-step enzymatic synthesis of the blue fluorescent noncanonical amino acid β-(1-azulenyl)-l-alanine (AzAla). By using an engineered tryptophan synthase β-subunit (TrpB), stereochemically pure AzAla can be synthesized at scale starting from commercially available azulene and l-serine. Mutation of a universally conserved catalytic glutamate in the active site to glycine has only a modest effect on native activity with indole but abolishes activity on azulene, suggesting that this glutamate activates azulene for nucleophilic attack by stabilization of the aromatic ion.
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