Absolute configuration of β - and α-asymmetric carbons within β-O-4-structures in hardwood lignin

Journal of Wood Chemistry and Technology

Volumn 35, Issue 1, 2014, Pages 8-16

  Akiyama, Takuya ^a   Magara, Kengo ^b   Meshitsuka, Gyosuke ^a   Lundquist, Knut ^c   Matsumoto, Yuji ^a  

^a UNIVERSITY OF TOKYO   (Japan)

^b FORESTRY AND FOREST PRODUCTS RESEARCH INSTITUTE   (Japan)

^c CHALMERS UNIVERSITY OF TECHNOLOGY   (Sweden)

Author keywords

8 O 4 structure; Angiosperms; Arylglycerol aryl ether; Birch; Diastereomer; Enantiomer; Erythro and threo isomers; Hardwood; Optical activity; Ozonation; Quinone methide; Radical coupling reaction; Syringyl and guaiacyl; O 4 structure

Indexed keywords

BIOCHEMISTRY; CHEMICAL REACTIONS; ENANTIOMERS; ETHERS; LIGNIN; OPTICAL MATERIALS; OZONE; OZONIZATION; PLANTS (BOTANY); QUINONE;

ANGIOSPERMS; ARYL ETHER; BIRCH; DIASTEREOMERS; ERYTHRO; GUAIACYL; OPTICAL ACTIVITY; QUINONE METHIDE; RADICAL COUPLING REACTIONS;

HARDWOODS;

BIOSYNTHESIS; CARBON; HARDWOODS; ISOMERS; LIGNINS;

EID: 84910663108     PISSN: 02773813     EISSN: 15322319     Source Type: Journal    
DOI: 10.1080/02773813.2014.892992     Document Type: Article

References (24)

1. Freudenberg, K.; Rasenack, D. d,l- ein weiteres Zwischenprodukt der Ligninbildung. Chem. Ber. 1953, 86(6), 755-758.
2. Bolzacchini, E.; Brunow, G.; Meinardi, S.; Orlandi, M.; Rindone, B.; Rummakko, P. Enantioselective synthesis of a benzofuranic neolignan by oxidative coupling. Tetrahedron Lett. 1998, 39(20), 3291-3294.
3. Orlandi, M.; Rindone, B.; Molteni, G.; Rummakko, P.; Brunow, G. Asymmetric biomimetic oxidations of phenols: The mechanism of diastereo- and enantioselective synthesis of dehydroconiferyl ferulate (DDF) and dehydrodiconiferyl alcohol (DDA). Tetrahedron 2001, 57(2), 371-378.
4. Davin, L.B.; Wang, H. -B.; Crowell, A.L.; Bedgar, D.L.; Martin, D.M.; Sarkanen, S.; Lewis, N.G. Stereoselective bimolecular phenoxy radical coupling by an auxiliary (dirigent) protein without an active center. Science 1997, 275(5298), 362-366.
5. Nimz, H.; Gaber, H. Isolierung von DLsyringaresinol aus Buchenholz. Chem. Ber. 1965, 98(2), 538-539.
6. Freudenberg, K.; Chen, C. -L.; Harkin, J.M.; Nimz, H.; Renner, H. Observations on lignin. Chem. Commun. 1965, 11, 224-225.
7. Ogiyama, K.; Kondo, T. On the pinoresinol type of structural units in lignin. Tetrahedron Lett. 1966, 7(19), 2083-2088; Erratum, Tetrahedron Lett. 1967, 8(32), 3144.
8. Ralph, J.; Peng, J.; Lu, F.; Hatfield, R.D.; Helm, R.F. Are lignins optically active? J. Agric. Food Chem. 1999, 47(8), 2991-2996.
9. Akiyama, T.; Magara, K.; Matsumoto, Y.; Meshitsuka, G.; Ishizu, A.; Lundquist, K. Proof of the presence of racemic forms of arylglycerol- β-aryl ether structure in lignin: Studies on the stereo structure of lignin by ozonation. J.Wood Sci. 2000, 46(5), 414-415.
10. Sato, Y.; Moriuchi, H.; Hishiyama, S.; Otsuka, Y.; Oshima, K.; Kasai, D.; Nakamura, M.; Ohara, S.; Katayama, Y.; Fukuda, M.; Masai, E. Identification of three alcohol dehydrogenase genes involved in the stereospecific catabolism of arylglycerol-β-aryl ether by Sphingobium sp. strain SYK-6. Appl. Environ. Microbiol. 2009, 75(16), 5195-5201.
11. Hishiyama, S.; Otsuka, Y.; Nakamura, M.; Ohara, S.; Kajita, S.; Masai, E.; Katayama, Y. Convenient synthesis of chiral lignin model compounds via optical resolution: Four stereoisomers of guaiacylglycerol- β-guaiacyl ether and both enantiomers of 3-hydroxy-1-(4-hydroxy-3-methoxyphenyl)- 2-(2-methoxy-phenoxy)-propan-1-one (erone). Tetrahedron Lett. 2012, 53(7), 842-845.
12. Alam, S.; Suzuki, T.; Katayama, T. Absolute configuration of syringylglycerol-8-O-4′- (sinapyl alcohol) ethers, neolignans as well as lignin substructure dimeric compounds in higher plants. Asian J. Biol. Sci. 2011, 4(2), 157-165.
13. Gall, D.L.; Kim, H.; Lu, F.; Donohue, T.J.; Noguera, D.R.; Ralph, J. Stereochemical features of glutathione-dependent enzymes in the Sphingobium sp. strain SYK-6 â -aryl etherase pathway. J. Biol. Chem. 2014, in press.
14. Akiyama, T.; Goto, H.; Nawawi, D.S.; Syafii, W.; Matsumoto Y.; Meshitsuka, G. Erythro/ threoratio of β-O-4 structures as an important structural characteristic of lignin. Part 4. Variation in the erythro/threo ratio in the softwood and hardwood lignins and its relation to syringyl/guaiacyl ratio. Holzforschung 2005, 59(3), 276-281.
15. Akiyama, T.; Sugimoto, T.; Matsumoto, Y.; Meshitsuka, G. Erythro/ threo ratio of β-O-4 structures as an important structural characteristic of lignin. I: Improvement of ozonation method for the quantitative analysis of lignin side-chain structure. J. Wood Sci. 2002, 48(3), 210-215.
16. 1H NMR spectral studies of lignins: Quantitative estimates of some types of structural elements. Nord. Pulp Paper Res. J. 1991, 6(3), 141-146.
17. 1H NMR spectral studies of lignins: Results regarding the occurrence of β-5 structures, β-β structures, non-cyclic benzyl aryl ethers, carbonyl group and phenolic groups. Nord. Pulp Paper Res. J. 1992, Q7(1), 4-8, 16.
18. Ralph, J.; Lundquist, K.; Brunow, G.; Lu, F.; Kim, H.; Schatz, P.F.; Marita, J.M.; Hatfield, R.D.; Ralph, S.A.; Christensen, J.H.; Boerjan, W. Lignins: Natural polymers from oxidative coupling of 4-hydroxyphenylpropanoids. Phytochem. Rev. 2004, 3(1-2), 29-60.
19. 1H NMR spectroscopic data for lignin model compounds. Acta Chem. Scand. 1979, 33B(6), 418-420.
20. Nimz, H.H.; Tschirner, U.; Stähle, M.; Lehmann, R.; Schlosser, M. Carbon-13 NMR spectra of lignins. 10. Comparison of structural units in spruce and beech lignin. J. Wood Chem. Technol. 1984, 4(3), 265-284.
21. 13C NMR using the 2D INADEQUATE experiment. Magn. Reson. Chem. 1988, 36(8), 597-600.
22. Matsumoto, Y.; Ishizu, A.; Nakano, J. Studies on chemical structure of lignin by ozonation. Holzforschung 1986, 40(Suppl.), 81-85.
23. Akiyama, T.; Matsumoto, Y.; Okuyama, T.; Meshitsuka, G. Erythro/ threo ratio of â -O- 4 structures as an important structural characteristic of lignin. Part 3: Ratio of erythro and threo forms of â -O-4 structures in tension wood lignin. Phytochem. 2003, 64(6), 1157-1162.
24. Brunow, G.; Karlsson, K.; Lundquist, K.; Sipilä, J. On the distribution of the diastereomers of the structural elements in lignins: The steric course of reactions mimicking lignin biosynthesis. Wood Sci. Technol. 1993, 27(4), 281-286.