Document Detail

Peroxidase-catalyzed desulfonation of 3,5-dimethyl-4-hydroxy and 3,5-dimethyl-4-aminobenzenesulfonic acids.
MedLine Citation:
PMID:  8267618     Owner:  NLM     Status:  MEDLINE    
Horseradish peroxidase (HRP), lignin peroxidase (LiP), and Mn(III)-malonate (a manganese peroxidase mimic) oxidized 3,5-dimethyl-4-hydroxybenzenesulfonic acid (I) to 2,6-dimethyl-1,4-benzoquinone (III) and 2,6-dimethyl-1,3,4-trihydroxybenzene (IV). Only LiP was efficient at oxidizing 3,5-dimethyl-4-aminobenzenesulfonic acid (II); LiP oxidized II to 2,6-dimethyl-1,4-benzoquinone (III) and 2,6-dimethyl-3-hydroxy-1,4-benzoquinone (V). In these reactions, the H2O2-oxidized peroxidases or Mn(III)-malonate oxidized the aromatic ring by two electrons to produce a cation. Nucleophilic attack by water on the sulfonic acid bearing carbon eliminated sulfonic acid as inorganic sulfite and produced 2,6-dimethyl-1,4-benzoquinone (III). Possible mechanisms for the formation of IV and V are discussed.
C Muralikrishna; V Renganathan
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Publication Detail:
Type:  Comparative Study; Journal Article; Research Support, U.S. Gov't, Non-P.H.S.    
Journal Detail:
Title:  Biochemical and biophysical research communications     Volume:  197     ISSN:  0006-291X     ISO Abbreviation:  Biochem. Biophys. Res. Commun.     Publication Date:  1993 Dec 
Date Detail:
Created Date:  1994-01-25     Completed Date:  1994-01-25     Revised Date:  2006-11-15    
Medline Journal Info:
Nlm Unique ID:  0372516     Medline TA:  Biochem Biophys Res Commun     Country:  UNITED STATES    
Other Details:
Languages:  eng     Pagination:  798-804     Citation Subset:  IM    
Department of Chemistry, Biochemistry, and Molecular Biology, Oregon Graduate Institute of Science & Technology, Portland 97291-1000.
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MeSH Terms
Basidiomycota / enzymology
Chromatography, High Pressure Liquid
Gas Chromatography-Mass Spectrometry
Horseradish Peroxidase / metabolism
Molecular Structure
Peroxidases / metabolism*
Substrate Specificity
Sulfanilic Acids / metabolism*
Reg. No./Substance:
0/Malonates; 0/Sulfanilic Acids; 141-82-2/malonic acid; 7439-96-5/Manganese; EC 1.11.1.-/Horseradish Peroxidase; EC 1.11.1.-/Peroxidases; EC 1.11.1.-/lignin peroxidase; EC peroxidase

From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine

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