DOE PAGES title logo U.S. Department of Energy
Office of Scientific and Technical Information

Title: Mechanistic Studies of a Skatole-Forming Glycyl Radical Enzyme Suggest Reaction Initiation via Hydrogen Atom Transfer

Journal Article · · Journal of the American Chemical Society

Not Available

Research Organization:
Harvard Univ., Cambridge, MA (United States)
Sponsoring Organization:
Alan T. Waterman; Howard Hughes Medical Institute (HHMI); NSF Graduate Research Fellowships; National Science Foundation (NSF); USDOE; USDOE Office of Science (SC), Basic Energy Sciences (BES)
Grant/Contract Number:
SC0019112
OSTI ID:
1872508
Journal Information:
Journal of the American Chemical Society, Journal Name: Journal of the American Chemical Society Journal Issue: 25 Vol. 144; ISSN 0002-7863
Publisher:
American Chemical SocietyCopyright Statement
Country of Publication:
United States
Language:
English

References (40)

Elucidating the Stereochemistry of Enzymatic Benzylsuccinate Synthesis with Chirally Labeled Toluene journal August 2016
Insight into the Mechanism of Phenylacetate Decarboxylase (PhdB), a Toluene‐Producing Glycyl Radical Enzyme journal November 2019
Computational estimation of the acidities of purines and indoles journal January 2019
The metabolic basis of 3-methylindole-induced pneumotoxicity journal January 1990
Modification of Cys-418 of pyruvate formate-lyase by methacrylic acid, based on its radical mechanism journal January 2000
Adenosylmethionine-dependent synthesis of the glycyl radical in pyruvate formate-lyase by abstraction of the glycine C-2 pro-S hydrogen atom. Studies of [2H]glycine-substituted enzyme and peptides homologous to the glycine 734 site. journal April 1994
The Radical S -Adenosyl- l -methionine Enzyme MftC Catalyzes an Oxidative Decarboxylation of the C-Terminus of the MftA Peptide journal May 2016
Mechanistic Investigation of Oxidative Decarboxylation Catalyzed by Two Iron(II)- and 2-Oxoglutarate-Dependent Enzymes journal February 2018
Photochemical Strategy for Carbon Isotope Exchange with CO 2 journal February 2021
The Glycyl Radical Enzyme Arylacetate Decarboxylase from Olsenella scatoligenes journal April 2021
Mechanistic Studies of Fatty Acid Activation by CYP152 Peroxygenases Reveal Unexpected Desaturase Activity journal December 2018
Deuterium Isotope Effects in the Unusual Addition of Toluene to Fumarate Catalyzed by Benzylsuccinate Synthase journal October 2006
The [4Fe-4S] 1+ Cluster of Pyruvate Formate-Lyase Activating Enzyme Generates the Glycyl Radical on Pyruvate Formate-Lyase:  EPR-Detected Single Turnover journal August 2000
Electron-Nuclear Double Resonance Spectroscopic Evidence That S -Adenosylmethionine Binds in Contact with the Catalytically Active [4Fe−4S] + Cluster of Pyruvate Formate-Lyase Activating Enzyme journal March 2002
Mechanism of Benzylsuccinate Synthase Probed by Substrate and Isotope Exchange journal November 2006
Structural Basis for a Kolbe-Type Decarboxylation Catalyzed by a Glycyl Radical Enzyme journal September 2011
Catalytic Mechanism of the Glycyl Radical Enzyme 4-Hydroxyphenylacetate Decarboxylase from Continuum Electrostatic and QC/MM Calculations journal September 2013
Chemoselective Catalytic α-Oxidation of Carboxylic Acids: Iron/Alkali Metal Cooperative Redox Active Catalysis journal February 2020
The Elusive 5′-Deoxyadenosyl Radical: Captured and Characterized by Electron Paramagnetic Resonance and Electron Nuclear Double Resonance Spectroscopies journal July 2019
Substrate-Triggered Formation of a Peroxo-Fe 2 (III/III) Intermediate during Fatty Acid Decarboxylation by UndA journal September 2019
Indoleacetate decarboxylase is a glycyl radical enzyme catalysing the formation of malodorant skatole journal October 2018
Highly accurate protein structure prediction with AlphaFold journal July 2021
Discovery of enzymes for toluene synthesis from anoxic microbial communities journal March 2018
Structure–function relationships of radical SAM enzymes journal April 2020
In vitro Characterization of Phenylacetate Decarboxylase, a Novel Enzyme Catalyzing Toluene Biosynthesis in an Anaerobic Microbial Community journal August 2016
p -Hydroxyphenylacetate decarboxylase from Clostridium difficile : A novel glycyl radical enzyme catalysing the formation of journal March 2001
A glycyl radical enzyme enables hydrogen sulfide production by the human intestinal bacterium Bilophila wadsworthia journal February 2019
Two radical-dependent mechanisms for anaerobic degradation of the globally abundant organosulfur compound dihydroxypropanesulfonate journal June 2020
The free radical in pyruvate formate-lyase is located on glycine-734. journal February 1992
New tricks for the glycyl radical enzyme family journal September 2017
SWISS-MODEL: homology modelling of protein structures and complexes journal May 2018
ColabFold - Making protein folding accessible to all posted_content February 2022
Subunit composition of the glycyl radical enzyme p-hydroxyphenylacetate decarboxylase: A small subunit, HpdC, is essential for catalytic activity journal May 2004
Free-Radical Side-Chain Bromination of Alkylaromatics in Supercritical Carbon Dioxide journal January 1994
Mechanism and dynamics of fatty acid photodecarboxylase journal April 2021
3-Methylindole (skatole) and indole production by mixed populations of pig fecal bacteria journal August 1995
Structure and Function of 4-Hydroxyphenylacetate Decarboxylase and Its Cognate Activating Enzyme journal January 2016
Revised Estimates for the Number of Human and Bacteria Cells in the Body journal August 2016
Skatole (3-Methylindole) Is a Partial Aryl Hydrocarbon Receptor Agonist and Induces CYP1A1/2 and CYP1B1 Expression in Primary Human Hepatocytes journal May 2016
Modeling of the Reaction Mechanism of Enzymatic Radical C–C Coupling by Benzylsuccinate Synthase journal April 2016