Document Detail

Synthesis and identification of 2,5-bis-(4-hydroxy-3-methoxyphenyl)-tetrahydrofuran-3,4-dicarboxylic acid, an unanticipated ferulate 8-8-coupling product acylating cereal plant cell walls.
MedLine Citation:
PMID:  16826306     Owner:  NLM     Status:  MEDLINE    
A new product implicated in cereal grain polysaccharide cross-linking has been authenticated by independent synthesis. Saponification of cereal grain fiber releases the RRRS/SSSR-isomer of 2,5-bis-(4-hydroxy-3-methoxyphenyl)-tetrahydrofuran-3,4-dicarboxylic acid. The parent ester logically derives from 8-8-coupling of ferulate followed by water addition to one of the incipient quinone methide moieties and internal trapping of the other. The finding adds complexity to the analysis of plant cell wall cross-linking, but provides clues to important polysaccharide cross-linking pathways occurring in planta.
Paul F Schatz; John Ralph; Fachuang Lu; Ilia A Guzei; Mirko Bunzel
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Publication Detail:
Type:  Journal Article; Research Support, U.S. Gov't, Non-P.H.S.     Date:  2006-06-15
Journal Detail:
Title:  Organic & biomolecular chemistry     Volume:  4     ISSN:  1477-0520     ISO Abbreviation:  Org. Biomol. Chem.     Publication Date:  2006 Jul 
Date Detail:
Created Date:  2006-07-07     Completed Date:  2006-09-22     Revised Date:  2006-11-15    
Medline Journal Info:
Nlm Unique ID:  101154995     Medline TA:  Org Biomol Chem     Country:  England    
Other Details:
Languages:  eng     Pagination:  2801-6     Citation Subset:  IM    
US Dairy Forage Research Center, USDA-Agricultural Research Service, 1925 Linden Drive West, Madison, WI 53706, USA.
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MeSH Terms
Carboxylic Acids / chemical synthesis*,  chemistry*
Cell Wall / chemistry*
Cereals / chemistry*
Coumaric Acids / chemistry*
Crystallography, X-Ray
Furans / chemical synthesis*,  chemistry*
Molecular Structure
Reg. No./Substance:
0/2,5-bis-(4-hydroxy-3-methoxyphenyl)-tetrahydrofuran-3,4-dicarboxylic acid; 0/Carboxylic Acids; 0/Coumaric Acids; 0/Furans; 1135-24-6/ferulic acid

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