Document Detail


Transformation of 3,5-dimethoxy,4-hydroxy cinnamic acid by polyphenol oxidase from the fungus Trametes versicolor: product elucidation studies.
MedLine Citation:
PMID:  10099249     Owner:  NLM     Status:  MEDLINE    
Abstract/OtherAbstract:
Sinapic acid (SA), 3,5-dimethoxy,4-hydroxy cinnamic acid, was incubated with a crude polyphenol oxidase from the fungus Trametes versicolor. Some products of this transformation were isolated and their structures identified using mass spectrometry, nuclear magnetic resonance and Fourier transform infrared spectroscopy, and X-ray crystallography. It was found that the enzymatic oxidation of SA includes two distinct phases. In the initial phase SA is enzymatically transformed to r-1H-2c,6c-bis-(4'-hydroxy-3', 5'-dimethoxyphenyl)-3,7-dioxabicyclo-[3,3,0]-octane-4,8-dione, dehydrodisinapic acid dilactone. The mechanism of this reaction may involve coupling of two phenoxy radicals by the beta-beta mode and subsequent intramolecular nucleophilic attack. In the second phase dehydrodisinapic acid dilactone is transformed by polyphenol oxidase into several intermediate products, including 4-(4-(3, 5-dimethoxy-4-oxo-2,5-cyclohexadienyliden)-1, 4-dihydroxy-(E)-2-butenylidene)-2,6-dimethoxy-2, 5-cyclohexadien-1-one. The final product of the overall transformation of SA is 2,6-dimethoxy-p-benzoquinone. The obtained results were used to propose a part of the transformation pathway for the enzymatic oxidation of SA by polyphenol oxidase.
Authors:
K Lacki; Z Duvnjak
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Publication Detail:
Type:  Journal Article    
Journal Detail:
Title:  Biotechnology and bioengineering     Volume:  57     ISSN:  0006-3592     ISO Abbreviation:  Biotechnol. Bioeng.     Publication Date:  1998 Mar 
Date Detail:
Created Date:  1999-05-03     Completed Date:  1999-05-03     Revised Date:  2006-11-15    
Medline Journal Info:
Nlm Unique ID:  7502021     Medline TA:  Biotechnol Bioeng     Country:  UNITED STATES    
Other Details:
Languages:  eng     Pagination:  694-703     Citation Subset:  IM    
Copyright Information:
Copyright 1998 John Wiley & Sons, Inc.
Affiliation:
Department of Chemical Engineering, University of Ottawa, Ottawa, Ontario, Canada K1N 6N5.
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MeSH Terms
Descriptor/Qualifier:
Basidiomycota / enzymology*
Bicyclo Compounds, Heterocyclic / chemistry,  metabolism
Catechol Oxidase / chemistry,  metabolism*
Choline / analogs & derivatives,  chemistry,  metabolism
Chromatography, High Pressure Liquid
Coumaric Acids / chemistry*,  metabolism*
Lactones / chemistry,  metabolism
Mass Spectrometry / methods
Chemical
Reg. No./Substance:
0/Bicyclo Compounds, Heterocyclic; 0/Coumaric Acids; 0/Lactones; 0/dehydrodisinapic acid dilactone; 18696-26-9/sinapine; 530-59-6/sinapinic acid; 62-49-7/Choline; EC 1.10.3.1/Catechol Oxidase

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


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