ArticleJournal of the American Chemical Society2006
Mechanism of benzylsuccinate synthase probed by substrate and isotope exchange.
Article in Journal of the American Chemical Society, 2006. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 13 papers.
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Who cites it
13 citing papers in PubMed, 35 citations in OpenAlex.
- The structural basis of malodorant skatole formation by the glycyl radical enzyme indoleacetate decarboxylase.Proceedings of the National Academy of Sciences of the United States of America · 2026Article
- Nature's Anaerobic Toolkit: Glycyl Radical Enzymes and Their Expanding Functional and Mechanistic Diversity.Biochemistry · 2026Review
- The Structural Basis of Malodorant Skatole Formation by the Glycyl Radical Enzyme Indoleacetate Decarboxylase.bioRxiv : the preprint server for biology · 2026Article
- Structural basis for anaerobic alkane activation by a multisubunit glycyl radical enzyme.Proceedings of the National Academy of Sciences of the United States of America · 2025Article
- Development of aniScience · 2023Article
- Mechanistic Studies of a Skatole-Forming Glycyl Radical Enzyme Suggest Reaction Initiation via Hydrogen Atom Transfer.Journal of the American Chemical Society · 2022Article
- New tricks for the glycyl radical enzyme family.Critical reviews in biochemistry and molecular biology · 2017Review
- Substrate-bound structures of benzylsuccinate synthase reveal how toluene is activated in anaerobic hydrocarbon degradation.The Journal of biological chemistry · 2015Article
- Versatile transformations of hydrocarbons in anaerobic bacteria: substrate ranges and regio- and stereo-chemistry of activation reactions.Frontiers in microbiology · 2015Article
- Structures of benzylsuccinate synthase elucidate roles of accessory subunits in glycyl radical enzyme activation and activity.Proceedings of the National Academy of Sciences of the United States of America · 2014Article
- Mechanistic studies of the radical SAM enzyme spore photoproduct lyase (SPL).Biochimica et biophysica acta · 2012Review
- Adenosyl radical: reagent and catalyst in enzyme reactions.Chembiochem : a European journal of chemical biology · 2010Review
- Subunit structure of benzylsuccinate synthase.Biochemistry · 2009Article
Corrections and comments
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Authors and funding
2 authors at 1 institution in 1 country.
Funding
Abstract
Benzylsuccinate synthase catalyzes the first step in the anaerobic metabolism of toluene through an unusual reaction in which toluene is added to fumarate to produce (R)-benzylsuccinate. We have exploited the broad substrate range of the enzyme to demonstrate that the enzyme can catalyze the exchange of p-cresol with the benzyl portion of benzylsuccinate to form (4-hydroxybenzyl)-succinate, indicating that the reverse reaction (disproportionation of benzylsuccinate to toluene and fumarate) must have occurred. Even though the equilibrium constant for the reverse reaction is extremely unfavorable, Keq approximately 8 x 10-11 M at 4 degrees C, the enzyme catalyzes the reverse reaction at a rate only 250-fold slower than the forward reaction. Furthermore, using deuterium-labeled benzylsuccinate we observe partial exchange of deuterium with the solvent. This provides the first direct evidence that the migrating hydrogen is transferred to a labile site on the protein during catalysis, which is consistent with the participation of the proposed active-site cysteine residue in the mechanism of BSS.
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