Identification of Side-Chain Structures in a Poplar Lignin Using Three-Dimensional HMQC-HOHAHA NMR Spectroscopy

Journal of Agricultural and Food Chemistry

Volumn 46, Issue 12, 1998, Pages 5113-5117

  Ämmälahti, Erja ^a   Brunow, Gösta ^a   Bardet, Michel ^b   Robert, Danielle ^c   Kilpeläinen, Ilkka ^d  

^a UNIVERSITY OF HELSINKI   (Finland)

^b CEA GRENOBLE   (France)

^c CENTRE DE RECHERCHES SUR LES MACROMOLÉCULES VÉGÉTALES CERMAV CNRS   (France)

^d UNIVERSITY OF HELSINKI   (Finland)

Author keywords

3D HMQC HOHAHA; Lignin; NMR

Indexed keywords

POPULUS BEROLINENSIS;

EID: 0542369702     PISSN: 00218561     EISSN: None     Source Type: Journal    
DOI: 10.1021/jf980249o     Document Type: Article

References (27)

1. Adler, E. Lignin chemistry - past, present and future. Wood Sci. Technol. 1977, 11, 169-218.
2. 13C Enriched Wood for Structural NMR Investigation of Wood and Wood components, Cellulose and Lignin, in Solid and in Solution. Holzforschung 1986, 40 (Suppl.), 17-24.
3. Björkman, A. Studies on finely divided wood. Part I. Extraction of lignin with neutral solvents. Svensk Papperstidn. 1956, 59, 477.
4. Brunow, G.; Kilpeläinen, I.; Sipilä, J.; Syrjänen, K.; Karhunen, P.; Setalä, H.; Rummakko, P. Oxidative Coupling of Phenols and the Biosynthesis of Lignin. In Lignin and Lignan Biosynthesis; Lewis, N. G., Sarkanen, S., Eds.; ACS Symposium Series 697; American Chemical Society: Wahington, DC, 1998a; pp 131-147.
5. Brunow, G.; Ämmälahti, E.; Niemi, T.; Sipila, J.; Simola, L. K.; Kilpeläinen, I. Labeling of a lignin from suspension cultures of Picea abies. Phytochemistry 1998b, 47, 1495-1500.
6. Ede, R. M.; Brunow, G. Application of Two-Dimensional Home and Heteronuclear NMR Spectroscopy to Wood Lignin Structure Determination. J. Org. Chem. 1992, 57, 1477-1480.
7. 1H Chemical Shift Correlation and J-Resolved NMR Studies on Isolated and Synthetic Lignins. Holzforschung 1990, 44, 95-101.
8. Fukagawa, N.; Meshitsuka, G.; Ishizu, A. A Two-Dimensional NMR Study of Birch Milled Wood Lignin. J. Wood Chem. Technol. 1991, 11, 373-396.
9. 1H Spin System Identification in Macromolecules. J. Am. Chem. Soc. 1988, 110, 7870-7872.
10. 13C NMR "Inadequate" experiment to lignin, a natural polymer. Tetrahedron Lett. 1985, 26, 2671-2674.
11. Karhunen, P.; Rummakko, P.; Sipilä, J.; Brunow, G.; Kilpeläinen, I. Dibenzodioxocins; A Novel Type Of Linkage In Softwood Lignins. Tetrahedron Lett. 1995, 36, 169-170.
12. Kilpeläinen, I. Synthesis of lignin model compounds and analysis of lignin structure by NMR spectroscopy. Ann. Acad. Sci., Ser. A II 1994, 1-373.
13. Kilpeläinen, I.; Sipilä, J.; Brunow, G.; Lundquist, K. Application of Two-Dimensional NMR Spectroscopy to Wood Lignin Structure Determination and Identification of Some Minor Structural Units of Hard-and Softwood Lignins. J. Agric. Food Chem. 1994a, 42, 2790-2794.
14. Kilpeläinen, I.; Ämmälahti, E.; Brunow, G.; Robert, D. Application of Three-Dimensional HMQC-HOHAHA NMR Spectroscopy to Wood Lignin, a Natural Polymer. Tetrahedron Lett. 1994b, 35, 9267-9270.
15. Lai, Y. Z.; Sarkanen, K. V. Isolation and structural studies. In Lignins, Occurrence, Formation, Structure and Reactions; Sarkanen, K. V., Ludwig, C. H., Eds.; Wiley-Interscience: New York, 1971; pp 214-215.
16. 13C. Holzforschung 1983, 37, 217-224.
17. Lapierre, C.; Monties, B.; Guittet, E.; Lallemand, J. Y. Photosynthetically Carbon-13 Labeled Poplar Lignin: Carbon-13 Experiments. Holzforschung 1984, 38, 333-342.
18. 13C NMR Spectroscopy. J. Chem. Soc., Chem. Commun. 1988, 1626-1628.
19. 1H NMR Spectroscopy. Acta Chem. Scand. 1980, B34, 21-26.
20. 1H NMR spectral studies of lignins. Results regarding the occurrence of β-5 structures, β-β structures, non-cyclic benzyl aryl ethers, carbonyl groups and phenolic groups. Nord. Pulp Pap. Res. J. 1992, 7, 4-8.
21. Ralph, J.; Mackay, J. J.; Hatfield, R. D.; O'Malley, D. M.; Whetten, R. W.; Sederoff, R. R. Abnormal Lignin in a Loblolly Pine Mutant. Science 1997, 277, 235-239.
22. Robert, D. Carbon-13 Nuclear magnetic resonance Spectroscopy. In Methods in Lignin Chemistry; Lin, S. Y., Dence, C. W., Eds.; Springer-Verlag: Heidelberg, 1992; pp 250-265.
23. Sarkanen, K. V.; Ludwig, C. H. Lignins, Occurrence, Formation, Structure and Reactions; Wiley-Interscience: New York, 1971.
24. 12 through the Use of New Two-Dimensional NMR Experiments. J. Am. Chem. Soc. 1986, 108, 4285-4294.
25. Whiting, P.; Goring, D. A. I. The morphological origin of milled wood lignin. Svensk Papperstidn. 1981, 84, R120-R122.
26. Wijmenga, S. S.; Hallenga, K.; Hilbers, C. W. A Three-Dimensional Heteronuclear Multiple-Quantum Coherence Homonuclear Hartmann-Hahn Experiment. J. Magn. Reson. 1989, 84, 634-642.
27. Yoshikawa, K.; Kinoshita, H.; Arihara, S. Woorenol, a Novel Sesquineolignan with a Unique Spiro Skeleton, from the Rhizomes of Coptis japonica var. dissecta. J. Nat. Prod. 1997, 60, 511-513.