ArticleJournal of the American Chemical Society2016
NMR Crystallography of a Carbanionic Intermediate in Tryptophan Synthase: Chemical Structure, Tautomerization, and Reaction Specificity.
Article in Journal of the American Chemical Society, 2016. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 37 papers.
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37 citing papers in PubMed, 72 citations in OpenAlex.
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- Rotameric Heterogeneity of Conserved Tryptophan Is Responsible for Reduced Photochemical Quantum Yield in Cyanobacteriochrome Slr1393g3.Chemphyschem : a European journal of chemical physics and physical chemistry · 2025Article
- The interplay of density functional selection and crystal structure for accurate NMR chemical shift predictions.Faraday discussions · 2025Article
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- Unveiling the topology of partially disordered micro-crystalline nitro-perylenediimide with X-aggregate stacking: an integrated approach.Chemical science · 2024Article
- Engineered Biocatalytic Synthesis of β-N-Substituted-α-Amino Acids.Angewandte Chemie (International ed. in English) · 2023Article
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- Investigation of β-Substitution Activity of O-Acetylserine Sulfhydrolase from Citrullus vulgaris.Chembiochem : a European journal of chemical biology · 2022Article
- Aromatic L-amino acid decarboxylases: mechanistic features and microbial applications.Applied microbiology and biotechnology · 2022Review
- Discovery of antimicrobial agent targeting tryptophan synthase.Protein science : a publication of the Protein Society · 2022Article
- Atomic-resolution chemical characterization of (2x)72-kDa tryptophan synthase via four- and five-dimensionalProceedings of the National Academy of Sciences of the United States of America · 2022Article
- Imaging active site chemistry and protonation states: NMR crystallography of the tryptophan synthase α-aminoacrylate intermediate.Proceedings of the National Academy of Sciences of the United States of America · 2022Article
- Allosteric regulation of substrate channeling:Frontiers in molecular biosciences · 2022Review
- Fungicidal amphotericin B sponges are assemblies of staggered asymmetric homodimers encasing large void volumes.Nature structural & molecular biology · 2021Article
- Mutation of βGln114 to Ala Alters the Stabilities of Allosteric States in Tryptophan Synthase Catalysis.Biochemistry · 2021Article
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11 authors at 1 institution in 1 country.
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Abstract
Carbanionic intermediates play a central role in the catalytic transformations of amino acids performed by pyridoxal-5'-phosphate (PLP)-dependent enzymes. Here, we make use of NMR crystallography-the synergistic combination of solid-state nuclear magnetic resonance, X-ray crystallography, and computational chemistry-to interrogate a carbanionic/quinonoid intermediate analogue in the β-subunit active site of the PLP-requiring enzyme tryptophan synthase. The solid-state NMR chemical shifts of the PLP pyridine ring nitrogen and additional sites, coupled with first-principles computational models, allow a detailed model of protonation states for ionizable groups on the cofactor, substrates, and nearby catalytic residues to be established. Most significantly, we find that a deprotonated pyridine nitrogen on PLP precludes formation of a true quinonoid species and that there is an equilibrium between the phenolic and protonated Schiff base tautomeric forms of this intermediate. Natural bond orbital analysis indicates that the latter builds up negative charge at the substrate C
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