ArticleBiochemistry2009
Crystallographic, spectroscopic, and computational analysis of a flavin C4a-oxygen adduct in choline oxidase.
Article in Biochemistry, 2009. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 24 papers.
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Who cites it
24 citing papers in PubMed.
- Electrochemical Choline Sensing: Biological Context, Electron Transfer Pathways and Practical Design Strategies.Biomolecules · 2025Review
- Unifying and versatile features of flavin-dependent monooxygenases: Diverse catalysis by a common C4a-(hydro)peroxyflavin.The Journal of biological chemistry · 2023Review
- Ultrafast photooxidation of protein-bound anionic flavin radicals.Proceedings of the National Academy of Sciences of the United States of America · 2022Article
- Structural and chemical trapping of flavin-oxide intermediates reveals substrate-directed reaction multiplicity.Protein science : a publication of the Protein Society · 2020Article
- Flavinium Catalysed Photooxidation: Detection and Characterization of Elusive Peroxyflavinium Intermediates.Angewandte Chemie (International ed. in English) · 2019Review
- Comparative Computational Approach To Study Enzyme Reactions Using QM and QM-MM Methods.ACS omega · 2018Article
- Enzymatic control of dioxygen binding and functionalization of the flavin cofactor.Proceedings of the National Academy of Sciences of the United States of America · 2018Article
- Modulation of the flavin-protein interactions in NADH peroxidase and mercuric ion reductase: a resonance Raman study.European biophysics journal : EBJ · 2018Article
- Crystal Structure of Alcohol Oxidase from Pichia pastoris.PloS one · 2016Article
- Metalloproteins containing cytochrome, iron-sulfur, or copper redox centers.Chemical reviews · 2014Review
- Human choline dehydrogenase: medical promises and biochemical challenges.Archives of biochemistry and biophysics · 2013Review
- Oxidation mode of pyranose 2-oxidase is controlled by pH.Biochemistry · 2013Article
- Article
- Flavoenzymes: versatile catalysts in biosynthetic pathways.Natural product reports · 2013Review
- Quaternary ammonium oxidative demethylation: X-ray crystallographic, resonance Raman, and UV-visible spectroscopic analysis of a Rieske-type demethylase.Journal of the American Chemical Society · 2012Article
- Article
- Hydrogen peroxide elimination from C4a-hydroperoxyflavin in a flavoprotein oxidase occurs through a single proton transfer from flavin N5 to a peroxide leaving group.The Journal of biological chemistry · 2011Article
- Correlated single-crystal electronic absorption spectroscopy and X-ray crystallography at NSLS beamline X26-C.Journal of synchrotron radiation · 2011Review
- Revealing low-dose radiation damage using single-crystal spectroscopy.Journal of synchrotron radiation · 2011Article
- Single-crystal Raman spectroscopy and X-ray crystallography at beamline X26-C of the NSLS.Journal of synchrotron radiation · 2011Article
Corrections and comments
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Authors and funding
5 authors.
Funding
Abstract
Flavin C4a-OO(H) and C4a-OH adducts are critical intermediates proposed in many flavoenzyme reaction mechanisms, but they are rarely detected even by rapid transient kinetics methods. We observe a trapped flavin C4a-OH or C4a-OO(H) adduct by single-crystal spectroscopic methods and in the 1.86 A resolution X-ray crystal structure of choline oxidase. The microspectrophotometry results show that the adduct forms rapidly in situ at 100 K upon exposure to X-rays. Density functional theory calculations establish the electronic structures for the flavin C4a-OH and C4a-OO(H) adducts and estimate the stabilization energy of several active site hydrogen bonds deduced from the crystal structure. We propose that the enzyme-bound FAD is reduced in the X-ray beam. The aerobic crystals then form either a C4a-OH or C4a-OO(H) adduct, but an insufficient proton inventory prevents their decay at cryogenic temperatures.
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