ArticleThe Journal of organic chemistry2018
Improved Synthesis of 4-Cyanotryptophan and Other Tryptophan Analogues in Aqueous Solvent Using Variants of TrpB from Thermotoga maritima.
Article in The Journal of organic chemistry, 2018. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 38 papers.
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38 citing papers in PubMed, 72 citations in OpenAlex.
- Phage-assisted continuous evolution of enzymes for noncanonical tyrosine biosynthesis.Proceedings of the National Academy of Sciences of the United States of America · 2026Article
- Isosteric Engineering of Enzymes: Overcoming Activity-Stability Trade-Offs by Site-Selective CH → N Substitutions.Angewandte Chemie (International ed. in English) · 2026Article
- Phage-assisted continuous evolution of enzymes for noncanonical tyrosine biosynthesis.bioRxiv : the preprint server for biology · 2026Article
- Sequence-based generative AI design of versatile tryptophan synthases.Nature communications · 2026Article
- Active site diversification of a non-canonical amino acid decarboxylase by merging substrate multiplexed screening with computationally guided recombination.Protein science : a publication of the Protein Society · 2025Article
- Expanding the fluorescence toolkit: molecular design, synthesis and biological application of unnatural amino acids.Chemical science · 2025Review
- Promiscuity Guided Evolution of Decarboxylative Aldolases for Synthesis of Tertiary γ-Hydroxy Amino Acids.Angewandte Chemie (International ed. in English) · 2025Article
- Exploiting Archaeal/Thermostable Enzymes in Synthetic Chemistry: Back to the Future?ChemCatChem · 2024Article
- Tryptophan production by catalysis of a putative tryptophan synthase protein.Archives of microbiology · 2024Article
- A combinatorially complete epistatic fitness landscape in an enzyme active site.Proceedings of the National Academy of Sciences of the United States of America · 2024Article
- The β-subunit of tryptophan synthase is a latent tyrosine synthase.Nature chemical biology · 2024Article
- Cell cycle-linked vacuolar pH dynamics regulate amino acid homeostasis and cell growth.Nature metabolism · 2023Article
- Synthesis and Photophysical Properties of Charge-Transfer-Based Pyrimidine-Derived α-Amino Acids.The Journal of organic chemistry · 2023Article
- Synthesis and Fluorescence Properties of 4-Cyano and 4-Formyl Melatonin as Putative Melatoninergic Ligands.ACS omega · 2023Article
- Synthesis and Fluorescent Properties of Alkynyl- and Alkenyl-Fused Benzotriazole-Derived α-Amino Acids.The Journal of organic chemistry · 2023Article
- Biocatalytic Friedel-Crafts Reactions.ChemCatChem · 2022Review
- Versatile Vibrational Energy Sensors for Proteins.Angewandte Chemie (International ed. in English) · 2022Article
- In vivo hypermutation and continuous evolution.Nature reviews. Methods primers · 2022Article
- Fluorescent Amino Acid Initiated de novo Cyclic Peptides for the Label-Free Assessment of Cell Permeability*.ChemMedChem · 2021Article
- Asymmetric Alkylation of Ketones Catalyzed by Engineered TrpB.Angewandte Chemie (International ed. in English) · 2021Article
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5 authors at 1 institution in 1 country.
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Abstract
The use of enzymes has become increasingly widespread in synthesis as chemists strive to reduce their reliance on organic solvents in favor of more environmentally benign aqueous media. With this in mind, we previously endeavored to engineer the tryptophan synthase β-subunit (TrpB) for production of noncanonical amino acids that had previously been synthesized through multistep routes involving water-sensitive reagents. This enzymatic platform proved effective for the synthesis of analogues of the amino acid tryptophan (Trp), which are frequently used in pharmaceutical synthesis as well as chemical biology. However, certain valuable compounds, such as the blue fluorescent amino acid 4-cyanotryptophan (4-CN-Trp), could only be made in low yield, even at elevated temperature (75 °C). Here, we describe the engineering of TrpB from Thermotoga maritima that improved synthesis of 4-CN-Trp from 24% to 78% yield. Remarkably, although the final enzyme maintains high thermostability ( T
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