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

Paul F. Schatz; John Ralph; Fachuang Lu; Ilia A. Guzei; Mirko Bunzel

doi:10.1039/B605918J

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†

Paul F. Schatz,^a John Ralph,*^b Fachuang Lu,^c Ilia A. Guzei^d and Mirko Bunzel^e

* Corresponding authors

^a US Dairy Forage Research Center, USDA-Agricultural Research Service, 1925 Linden Drive West, Madison, WI, USA
E-mail: schatz@chem.wisc.edu
Fax: +1 (608) 890-0076
Tel: +1 (608) 890-0073

^b US Dairy Forage Research Center, USDA-Agricultural Research Service, 1925 Linden Drive West, Madison, WI, USA, USA
E-mail: jralph@wisc.edu
Fax: +1 (608) 890-0076
Tel: +1 (608) 890-0071

^c US Dairy Forage Research Centre, USDA-Agricultural Research Service, 1925 Linden Drive West, Madison, WI, USA, USA
E-mail: fachuanglu@wisc.edu
Fax: +1 (608) 890-0076
Tel: +1 (608) 890-0073

^d Deptartment of Chemistry, U. Wisconsin-Madison, 1101 University Ave., Madison, WI, USA
E-mail: iguzei@chem.wisc.edu
Fax: +1 (608) 263-4694
Tel: +1 (608) 262-0381

^e Institut für Biochemie und Lebensmittelchemie, U. Hamburg, Grindalallee 117, Hamburg, Germany
E-mail: Mirko.Bunzel@uni-hamburg.de
Fax: +49 (0)40-42-838-4342
Tel: +49 (0)40-42-838-4379

Abstract

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.

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DOI: https://doi.org/10.1039/B605918J
Article type: Paper
Submitted: 25 Apr 2006
Accepted: 24 May 2006
First published: 15 Jun 2006

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Org. Biomol. Chem., 2006,4, 2801-2806

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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

P. F. Schatz, J. Ralph, F. Lu, I. A. Guzei and M. Bunzel, Org. Biomol. Chem., 2006, 4, 2801 DOI: 10.1039/B605918J

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Organic & Biomolecular Chemistry

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†

Abstract

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Article information

Download Citation

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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

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