Preparation and relevance of a cross-coupling product between sinapyl alcohol and sinapyl p-hydroxybenzoate

Organic and Biomolecular Chemistry

Volumn 2, Issue 20, 2004, Pages 2888-2890

  Lu, Fachuang ^a,b   Ralph, John ^a,b   Morreel, Kris ^c   Messens, Eric ^c   Boerjan, Wout ^c  

^a U S DAIRY FORAGE RESEARCH CENTER   (United States)

^b UNIVERSITY OF WISCONSIN MADISON   (United States)

^c DEPARTMENT OF PLANT SYSTEMS BIOLOGY   (Belgium)

Author keywords

[No Author keywords available]

Indexed keywords

ACETYLATION; ENZYMES; ESTERS; GENES; MONOMERS; REACTION KINETICS;

CROSS-COUPLING REACTIONS; POPLAR PLANTS; SINAPYL ALCOHOL;

ALCOHOLS;

POPULUS BEROLINENSIS;

4 HYDROXYBENZOIC ACID ESTER; PHENYLPROPIONIC ACID DERIVATIVE; SINAPYL 4 HYDROXYBENZOATE; SINAPYL 4-HYDROXYBENZOATE; SINAPYL ALCOHOL;

ARTICLE; CHEMICAL MODEL; CHEMICAL STRUCTURE; CHEMISTRY;

MODELS, CHEMICAL; MOLECULAR STRUCTURE; PARABENS; PHENYLPROPIONATES;

EID: 8344234123     PISSN: 14770520     EISSN: None     Source Type: Journal    
DOI: 10.1039/b411428k     Document Type: Article

References (18)

1. W. Boerjan, J. Ralph and M. Baucher, Lignin Biosynthesis, Annu. Rev. Plant Biol., 2003, 54, 519.
2. J. Ralph, K. Lundquist, G. Brunow, F. Lu, H. Kim, P. F. Schatz, J. M. Marita, R. D. Hatfield, S. A. Ralph, J. H. Christensen and W. Boerjan, Lignins: natural polymers from oxidative coupling of 4-hydroxyphenylpropanoids, Phytochem. Rev., 2004, 3, in press.
3. J. C. del Rio, A. Gutierrez and A. T. Martinez, Identifying acetylated lignin units in non-wood fibers using pyrolysis-gas chromatography/mass spectrometry, Rapid Commun. Mass Spectrom., 2004, 18, 1181.
4. J. Ralph and F. Lu, The DFRC method for lignin analysis. Part 6. A modified method to determine acetate regiochemistry on native and isolated lignins, J. Agric. Food Chem., 1998, 46, 4616.
5. Y. Nakamura and T. Higuchi, Ester linkage of p-coumaric acid in bamboo lignin. II. Syntheses of coniferyl p-hydroxybenzoate and coniferyl p-coumarate as possible precursors of aromatic acid esters in lignin, Cellul. Chem. Technol., 1978, 12, 199.
6. F. Lu and J. Ralph, Preliminary evidence for sinapyl acetate as a lignin monomer in kenaf, Chem. Commun., 2002, 90.
7. J. Ralph, R. D. Hatfield, S. Quideau, R. F. Helm, J. H. Grabber and H.-J. G. Jung, Pathway of p-coumaric acid incorporation into maize lignin as revealed by NMR, J. Am. Chem. Soc., 1994, 116, 9448.
8. F. Lu and J. Ralph, Detection and determination of p-coumaroylated units in lignins, J. Agric. Food Chem., 1999, 47, 1988.
9. K. Morreel, J. Ralph, H. Kim, F. Lu, G. Goeminne, S. A. Ralph, E. Messens and W. Boerjan, Profiling of oligolignols reveals monolignol coupling conditions in lignifying poplar xylem, Plant Physiol., 2004, in press.
10. K. Morreel, J. Ralph, F. Lu, G. Goeminne, R. Busson, P. Herdewijn, J. L. Goeman, J. Van der Eycken, W. Boerjan and E. Messens, Phenolic profiling of COMT-deficient poplar reveals novel benzodioxane oligolignols, Plant Physiol., 2004, in press.
11. K. Syrjanen and G. Brunow, Regioselectivity in lignin biosynthesis. The influence of dimerization and cross-coupling, J. Chem. Soc., Perkin Trans. 1, 2000, 183.
12. F. Lu and J. Ralph, Highly selective syntheses of coniferyl and sinapyl alcohols, J. Agric. Food Chem., 1998, 46, 1794.
13. K. Freudenberg and A. C. Neish. Constitution and Biosynthesis of Lignin, Springer-Verlag, Berlin-Heidelberg-New York, 1968.
14. M. Tanahashi, H. Takeuchi and T. Higuchi, Dehydrogenative polymerization of 3,5-disubstituted p-coumaryl alcohols, Wood Res., 1976, 61, 44.
15. H. Meyermans, K. Morreel, C. Lapierre, B. Pollet, A. De Bruyn, R. Busson, P. Herdewijn, B. Devreese, J. Van Beeumen, J. M. Marita, J. Ralph, C. Chen, B. Burggraeve, M. Van Montagu, E. Messens and W. Boerjan, Modifications in lignin and accumulation of phenolic glucosides in poplar xylem upon down-regulation of caffeoyl-coenzyme A O-methyltransferase, an enzyme involved in lignin biosynthesis, J. Biol. Chem., 2000, 275, 36899.
16. H. Lee, N. Watanabe, T. Sasaya and S. Ozawa, Extractives of short-rotation hardwood species. I. Phenolics of the wood of Salix sachalinensis Fr. Schm, Mokuzal Gakkaishi, 1993, 39, 1409.
17. J. Ralph and B. R. Adams, Determination of the conformation and isomeric composition of lignin model quinone methides by NMR, J. Wood Chem. Technol., 1983, 3, 183.
18. T. Zinke and O. Hahn, Über die Einwirkung von Brom und von Chlor auf Phenole: Substitutioasprodukten, Pseudobromide and Pseudochloride; K. Über die Einwirkung von Brom auf Isoeugenol, Justus Liebigs Ann. Chem., 1903, 329, 1.