536-28-7

Basic information

• Product Name: Ethionamide Sulfoxide
• Synonyms: Ethionamide Sulfoxide;2-Ethyl-4-pyridinecarbothioaMide S-Oxide;2-EthylthioisonicotinaMide S-Oxide;EthionaMide-S-oxide;Ethionamide Sulfoxide D5
• CAS NO: 536-28-7
• Molecular Formula: C8H10N2OS
• Molecular Weight: 182.2428
• Product Categories: Intermediates & Fine Chemicals;Metabolites & Impurities;Pharmaceuticals;Sulfur & Selenium Compounds
• Mol File: 536-28-7.mol
• Article Data: 2

Chemical Properties

• Melting Point: 138-140?C
• Appearance: /
• Density: 1.25g/cm³
• Refractive Index: 1.609
• Storage Temp.: Amber Vial, -20°C Freezer, Under Inert Atmosphere
• Solubility: DMSO (Slightly), Methanol (Slightly)
• CAS DataBase Reference: Ethionamide Sulfoxide(CAS DataBase Reference)
• NIST Chemistry Reference: Ethionamide Sulfoxide(536-28-7)
• EPA Substance Registry System: Ethionamide Sulfoxide(536-28-7)

Safety Data

• Hazardous Substances Data: 536-28-7(Hazardous Substances Data)

Usage

Chemical Properties

Yellow Solid

Uses

The major metabolite of Ethionamide.

InChI:InChI=1/C8H10N2OS/c1-2-7-5-6(3-4-10-7)8(9)12-11/h3-5H,2,9H2,1H3

Upstream product

• 536-33-4 ethionamide 

Relevant articles and documents

Characterization of a new Baeyer-Villiger monooxygenase and conversion to a solely N-or S-oxidizing enzyme by a single R292 mutation

Background Ar-BVMO is a recently discovered Baeyer-Villiger monooxygenase from the genome of Acinetobacter radioresistens S13 closely related to medically relevant ethionamide monooxygenase EtaA (prodrug activator) and capable of inactivating the imipenem antibiotic. Methods The co-substrate preference as well as steady-state and rapid kinetics studies of the recombinant purified protein were carried out using stopped-flow spectroscopy under anaerobic and aerobic conditions. Kd values were measured by isothermal calorimetry. Enzymatic activity was determined by measuring the amount of product formed using high pressure liquid chromatography or gas chromatography. Site-directed mutagenesis experiments were performed to decipher the role of the active site arginine-292. Results Ar-BVMO was found to oxidize ethionamide as well as linear ketones. Mechanistic studies on the wild type enzyme using stopped-flow spectroscopy allowed for the detection of the characteristic oxygenating C4a-(hydro)peroxyflavin intermediate, which decayed rapidly in the presence of the substrate. Replacement of arginine 292 in Ar-BVMO by glycine or alanine resulted in greatly reduced or no Baeyer-Villiger activity, respectively, demonstrating the crucial role of this residue in catalysis of ketone substrates. However, both the R292A and R292G mutants are capable of carrying out N- and S-oxidation reactions. Conclusions Substrate profiling of Ar-BVMO confirms its close relationship to EtaA; ethionamide is one of its substrates. The active site Arginine 292 is required for its Baeyer-Villiger activity but not for heteroatom oxidation. General significance A single mutation converts Ar-BVMO to a unique S- or N-monooxygenase, a useful biocatalyst for the production of oxidized metabolites of human drug metabolizing enzymes.