Regioselectivity in lignin biosynthesis. The influence of dimerization and cross-coupling

Journal of the Chemical Society, Perkin Transactions 1

Volumn , Issue 2, 2000, Pages 183-187

  Syrjänen, Kaisa ^a   Brunow, Gösta ^a  

^a UNIVERSITY OF HELSINKI   (Finland)

Author keywords

[No Author keywords available]

Indexed keywords

ACETIC ACID; BIOSYNTHESIS; DIFFUSION; DIMERIZATION; OXIDATION; PHENOLS; SOFTWOODS;

CROSS-COUPLING REACTIONS; REGIOSELECTIVITY;

LIGNIN;

ACETIC ACID; BIOSYNTHESIS; DIFFUSION; LIGNINS; OXIDATION; PHENOLS; SOFTWOODS;

EID: 0034695715     PISSN: 14704358     EISSN: None     Source Type: Journal    
DOI: 10.1039/a907919j     Document Type: Article

References (35)

1. K. Freudenberg and A. C. Neish, Constitution and Biosynthesis of Lignin, Springer-Verlag, Heidelberg, 1968, vol. 2.
2. K. V. Sarkanen and C. H. Ludwig, Lignins. Occurrence, Formation, Structure and Reactions, Wiley-Interscience, New York, 1971.
3. N. G. Lewis, Lignin and Lignan Biosynthesis, ed. N. G. Lewis and S. Sarkanen, ACS Symposium Series, American Chemical Society, Washington, DC, 1998, vol. 697, pp. 334-361.
4. E. Adler, Wood Sci. Technol., 1977, 11, 169.
5. J. Ralph, J. Peng, F. Lu, R. D. Hatfield and R. F. Helm, J. Agric. Food Chem., 1999, 47, 2991.
6. G. Brunow, I. Kilpeläinen, J. Sipilä, K. Syrjänen, P. Karhunen, H. Setälä and P. Rummakko, Lignin and Lignan Biosynthesis, ed. N. G. Lewis and S. Sarkanen, ACS Symposium Series, American Chemical Society, Washington, DC, 1998, vol. 697, p. 131.
7. K. Syrjänen and G. Brunow, J. Chem. Soc., Perkin Trans, 1, 1998, 3425.
8. F. Chioccara, S. Poli, B. Rindone, T. Pilati, G. Brunow, P. Pietikäinen and Harri Setälä, Acta Chem. Scand., Ser. B, 1993, 47, 610.
9. N. Terashima and R. H. Atalla, in 8th ISWPC, ed. anon., Gummerus Oy, Jyväskylä, Helsinki, 1995, vol. 1, p. 69.
10. S. Quideau and J. Ralph, Holzforschung, 1994, 48, 12.
11. J. C. Pew and W. J. Connors, Nature, 1967, 215, 623.
12. J. C. Pew and W. J. Connors, J. Org. Chem., 1969, 34, 580.
13. M. Erickson and G. E. Miksche, Acta Chem. Scand., Ser. B, 1972, 26, 3085.
14. M. Tanahashi and T. Higuchi, Wood Res., 1981, 67, 29.
15. L. L. Landucci and S. Ralph, Lignin and Lignan Biosynthesis, ed. N. G. Lewis and S. Sarkanen, ACS Symposium Series, American Chemical Society, Washington, DC, 1998, vol. 697, p. 148.
16. K. Freudenberg, Angew. Chem., 1956, 68, 508.
17. Y.-Z. Lai and K. V. Sarkanen, Cellul. Chem. Technol., 1975, 9, 239.
18. M. Tanahashi, H. Takeguchi and T. Higuchi, Wood Res., 1976, 61, 44.
19. E. Adler, G. Brunow and K. Lundquist, Holzforschung, 1987, 41, 199.
20. K. Freudenberg and H. H. Hübner, Chem. Ber., 1952, 85, 1181.
21. S. Quideau and J. Ralph, J. Agric. Food Chem., 1992, 40, 1108.
22. C. W. Bailey and C. W. Dence, Tappi, 1969, 52, 491
23. (Chem. Abstr., 1969, 71, 4053x).
24. M. Paulsson, S. Li, K. Lundquist, R. Simonson and U. Westermark, Nord. Pulp Pap. Res. J., 1996, 2, 109.
25. L. L. Landucci, S. A. Ralph and K. E. Hammel, Holzforschung, 1998, 52, 160.
26. F. Tiemann, Ber. Dtsch. Chem. Ges., 1891, 24, 2860.
27. J. C. Pew, J. Org. Chem., 1963, 28, 1048.
28. J. Sipilä and K. Syrjänen, Holzforschung, 1995, 49, 325.
29. F. Nakatsubo, K. Sato and T. Higuchi, Holzforschung, 1975, 29, 165.
30. F. Nakatsubo and T. Higuchi, Wood Res., 1980, 66, 23.
31. J.-P. Roblin, H. Duran, V. Banuls and L. Gorrichon, Bioorg. Med. Chem. Lett., 1996, 6, 2355.
32. R. Sterzycki, Synthesis, 1979, 724.
33. L. L. Landucci and S. Ralph, J. Wood Chem. Technol., 1997, 17, 361.
34. T. K. Kirk and G. Brunow, Methods Enzymol, 1988, 161, 65.
35. G. Cahiez and M. Alami, Encyclopedia of Reagents for Organic Synthesis, ed. L. A. Paquette, Wiley, Chichester, 1995, vol. 5, p. 3230.