Opposite stereoselectivities of dirigent proteins in Arabidopsis and Schizandra species

Journal of Biological Chemistry

Volumn 287, Issue 41, 2012, Pages 33957-33972

  Kim, Kye Won ^a   Moinuddin, Syed G A ^a   Atwell, Kathleen M ^a   Costa, Michael A ^a   Davin, Laurence B ^a   Lewis, Norman G ^a  

^a WASHINGTON STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ARABIDOPSIS; ARABIDOPSIS THALIANA; BIOCHEMICAL ANALYSIS; BIOCHEMICAL CONTROL; COUPLING MODE; ENANTIOSPECIFICITY; GLUCURONIDASE; IN-VITRO; IN-VITRO ANALYSIS; IN-VIVO; INTERMEDIA; OVER-EXPRESSION; RADICAL-RADICAL COUPLING; REPORTER GENE; ROOT TISSUES; SEQUENCE ANALYSIS; SITE DIRECTED MUTAGENESIS; STEREO-SELECTIVE; SUBSTRATE-BINDING SITES;

ENZYME ACTIVITY; PLANTS (BOTANY); STEREOSELECTIVITY;

RECOMBINANT PROTEINS;

DIRIGENT PROTEIN; PINORESINOL; UNCLASSIFIED DRUG; VEGETABLE PROTEIN;

ARABIDOPSIS; ARTICLE; CONTROLLED STUDY; ENZYME SPECIFICITY; ENZYME SUBSTRATE COMPLEX; GENE OVEREXPRESSION; IN VITRO STUDY; LOSS OF FUNCTION MUTATION; NONHUMAN; NUCLEOTIDE SEQUENCE; PLANT GROWTH; PLANT ROOT; PRIORITY JOURNAL; PROTEIN ANALYSIS; REPORTER GENE; RNA INTERFERENCE; SCHISANDRA CHINENSIS; SEQUENCE ANALYSIS; SEQUENCE HOMOLOGY; SITE DIRECTED MUTAGENESIS; STEREOCHEMISTRY;

ARABIDOPSIS; BINDING SITES; FURANS; LIGNANS; PLANT PROTEINS; PLANT ROOTS; SCHISANDRA; SEQUENCE HOMOLOGY, AMINO ACID; SPECIES SPECIFICITY; SUBSTRATE SPECIFICITY;

EID: 84867278908     PISSN: 00219258     EISSN: 1083351X     Source Type: Journal    
DOI: 10.1074/jbc.M112.387423     Document Type: Article

References (39)

1. Davin, L. B., Wang, H. B., Crowell, A. L., Bedgar, D. L., Martin, D. M., Sarkanen, S., and Lewis, N. G. (1997) Stereoselective bimolecular phenoxy radical coupling by an auxiliary (dirigent) protein without an active center. Science 275, 362-366 (Pubitemid 27051607)
2. Gang, D. R., Costa, M. A., Fujita, M., Dinkova-Kostova, A. T., Wang, H. B., Burlat, V., Martin, W., Sarkanen, S., Davin, L. B., and Lewis, N. G. (1999) Regiochemical control of monolignol radical coupling: a new paradigm for lignin and lignan biosynthesis. Chem. Biol. 6, 143-151 (Pubitemid 29363150)
3. Halls, S. C., and Lewis, N. G. (2002) Secondary and quaternary structures of the (+)-pinoresinol forming dirigent protein. Biochemistry 41, 9455-9461 (Pubitemid 34810021)
4. Halls, S. C., Davin, L. B., Kramer, D. M., and Lewis, N. G. (2004) Kinetic study of coniferyl alcohol radical binding to the (+)-pinoresinol forming dirigent protein. Biochemistry 43, 2587-2595 (Pubitemid 38327854)
5. Lin-gen, Z., Seligmann, O., Jurcic, K., and Wagner, H. (1982) Constituents of Daphne tangutica. Planta Med. 45, 172-176 (Pubitemid 13212168)
6. Ford, J. D., Huang, K. S., Wang, H. B., Davin, L. B., and Lewis, N. G. (2001) Biosynthetic pathway to the cancer chemopreventive secoisolariciresinol diglucoside-hydroxymethyl glutaryl ester-linked lignan oligomers in flax (Linum usitatissimum) seed. J. Nat. Prod. 64, 1388-1397 (Pubitemid 33116678)
7. Vassão, D. G., Kim, K.-W., Davin, L. B., and Lewis, N. G. (2010) in Comprehensive Natural Products Chemistry II (Townsend, C., and Ebizuka, Y., eds) pp. 815-928, Elsevier, Oxford, UK
8. Davin, L. B., Jourdes, M., Patten, A. M., Kim, K. W., Vassão, D. G., and Lewis, N. G. (2008) Dissection of lignin macromolecular configuration and assembly: comparison to related biochemical processes in allyl/propenyl phenol and lignan biosynthesis. Nat. Prod. Rep. 25, 1015-1090
9. Moinuddin, S. G. A., Jourdes, M., Laskar, D. D., Ki, C., Cardenas, C. L., Kim, K. W., Zhang, D., Davin, L. B., and Lewis, N. G. (2010) Insights into lignin primary structure and deconstruction from Arabidopsis thaliana COMT (caffeic acid O-methyl transferase) mutant Atomt1. Org. Biomol. Chem. 8, 3928-3946
10. Patten, A. M., Jourdes, M., Cardenas, C. L., Laskar, D. D., Nakazawa, Y., Chung, B. Y., Franceschi, V. R., Davin, L. B., and Lewis, N. G. (2010) Probing native lignin macromolecular configuration in Arabidopsis thaliana in specific cell wall types: further insights into limited substrate degeneracy and assembly of the lignins of ref8, fah 1-2 and C4H::F5H lines. Mol. BioSyst. 6, 499-515
11. Burlat, V., Kwon, M., Davin, L. B., and Lewis, N. G. (2001) Dirigent proteins and dirigent sites in lignifying tissues. Phytochemistry 57, 883-897 (Pubitemid 32607036)
12. Uzal, E. N., Gómez-Ros, L. V., Hernández, J. A., Pedreño, M. A., Cuello, J., and Ros Barceló, A. (2009) Analysis of the soluble cell wall proteome of gymnosperms. J. Plant Physiol. 166, 831-843
13. Liu, J., Stipanovic, R. D., Bell, A. A., Puckhaber, L. S., and Magill, C. W. (2008) Stereoselective coupling of hemigossypol to form (+)-gossypol in moco cotton is mediated by a dirigent protein. Phytochemistry 69, 3038-3042
14. Nakatsubo, T., Mizutani, M., Suzuki, S., Hattori, T., and Umezawa, T. (2008) Characterization of Arabidopsis thaliana pinoresinol reductase, a new type of enzyme involved in lignan biosynthesis. J. Biol. Chem. 283, 15550-15557
15. Pickel, B., Constantin, M. A., Pfannstiel, J., Conrad, J., Beifuss, U., and Schaller, A. (2010) An enantiocomplementary dirigent protein for the enantioselective laccase-catalyzed oxidative coupling of phenols. Angew. Chem. Int. Ed. Engl. 49, 202-204
16. Kim, S. J., Kim, M. R., Bedgar, D. L., Moinuddin, S. G. A., Cardenas, C. L., Davin, L. B., Kang, C., and Lewis, N. G. (2004) Functional reclassification of the putative cinnamyl alcohol dehydrogenase multigene family in Arabidopsis. Proc. Natl. Acad. Sci. U.S.A. 101, 1455-1460 (Pubitemid 38234176)
17. Moinuddin, S. G. A., Youn, B., Bedgar, D. L., Costa, M. A., Helms, G. L., Kang, C., Davin, L. B., and Lewis, N. G. (2006) Secoisolariciresinol dehydrogenase: mode of catalysis and stereospecificity of hydride transfer in Podophyllum peltatum. Org. Biomol. Chem. 4, 808-816 (Pubitemid 43289790)
18. Kim, K.-W., Franceschi, V. R., Davin, L. B., and Lewis, N. G. (2006) in Methods in Molecular Biology (Salinas, J., and Sanchez-Serrano, J. J., eds) pp. 263-273, Humana Press, Totowa, NJ
19. Kim, S. J., Kim, K. W., Cho, M. H., Franceschi, V. R., Davin, L. B., and Lewis, N. G. (2007) Expression of cinnamyl alcohol dehydrogenases and their putative homologues during Arabidopsis thaliana growth and development: lessons for database annotations? Phytochemistry 68, 1957-1974 (Pubitemid 47030614)
20. Gleave, A. P. (1992) A versatile binary vector system with a T-DNA organisational structure conducive to efficient integration of cloned DNA into the plant genome. Plant Mol. Biol. 20, 1203-1207
21. Karimi, M., Inzé, D., and Depicker, A. (2002) GATEWAY™ vectors for Agrobacterium-mediated plant transformation. Trends Plant Sci. 7, 193-195 (Pubitemid 36725938)
22. Czechowski, T., Stitt, M., Altmann, T., Udvardi, M. K., and Scheible, W. R. (2005) Genome-wide identification and testing of superior reference genes for transcript normalization in Arabidopsis. Plant Physiol. 139, 5-17 (Pubitemid 43951587)
23. Schneider, I. (1972) Cell lines derived from late embryonic stages of Drosophila melanogaster. J. Embryol. Exp. Morphol. 27, 353-365
24. Cedzich, A., Huttenlocher, F., Kuhn, B. M., Pfannstiel, J., Gabler, L., Stintzi, A., and Schaller, A. (2009) The protease-associated domain and C-terminal extension are required for zymogen processing, sorting within the secretory pathway, and activity of tomato subtilase 3 (SlSBT3). J. Biol. Chem. 284, 14068-14078
25. Grandori, R., Struck, K., Giovanielli, K., and Carey, J. (1997) A three-step PCR protocol for construction of chimeric proteins. Protein Eng. 10, 1099-1100 (Pubitemid 28004657)
26. Suzuki, S., Sakakibara, N., Umezawa, T., and Shimada, M. (2002) Survey and enzymatic formation of lignans of Anthriscus sylvestris. J. Wood Sci. 48, 536-541 (Pubitemid 37292765)
27. Katayama, T., Davin, L. B., and Lewis, N. G. (1992) An extraordinary accumulation of (-)-pinoresinol in cell-free extracts of Forsythia intermedia: evidence for enantiospecific reduction of (+)-pinoresinol. Phytochemistry 31, 3875-3881
28. Duffield, A. M. (1967) Mass spectrometric fragmentation of some lignans. J. Heterocycl. Chem. 4, 16-22
29. Yamamoto, S., Otto, A., and Simoneit, B. R. T. (2004) Lignans in resin of Araucaria angustifolia by gas chromatography/mass spectrometry. J. Mass Spectrom. 39, 1337-1347 (Pubitemid 39545983)
30. Sugiyama, M., and Kikuchi, M. (1993) Characterization of lariciresinol glucosides from Osmanthus asiaticus. Heterocycles 36, 117-121
31. Kim, M. K., Jeon, J. H., Fujita, M., Davin, L. B., and Lewis, N. G. (2002) The western red cedar (Thuja plicata) 8-8′ DIRIGENT family displays diverse expression patterns and conserved monolignol coupling specificity. Plant Mol. Biol. 49, 199-214 (Pubitemid 34414199)
32. Clough, S. J., and Bent, A. F. (1998) Floral dip: a simplified method for Agrobacterium-mediated transformation of Arabidopsis thaliana. Plant J. 16, 735-743
33. Pourcel, L., Routaboul, J. M., Kerhoas, L., Caboche, M., Lepiniec, L., and Debeaujon, I. (2005) TRANSPARENT TESTA10 encodes a laccase-like enzyme involved in oxidative polymerization of flavonoids in Arabidopsis seed coat. Plant Cell 17, 2966-2980
34. Turlapati, P. V., Kim, K. W., Davin, L. B., and Lewis, N. G. (2011) The laccase multigene family in Arabidopsis thaliana: towards addressing the mystery of their gene function(s). Planta 233, 439-470
35. Obayashi, T., Hayashi, S., Saeki, M., Ohta, H., and Kinoshita, K. (2009) ATTED-II provides coexpressed gene networks for Arabidopsis. Nucleic Acids Res. 37, D987-D991
36. Baerenfaller, K., Grossmann, J., Grobei, M. A., Hull, R., Hirsch-Hoffmann, M., Yalovsky, S., Zimmermann, P., Grossniklaus, U., Gruissem, W., and Baginsky, S. (2008) Genome-scale proteomics reveals Arabidopsis thaliana gene models and proteome dynamics. Science 320, 938-941 (Pubitemid 351929590)
37. Schmid, M., Davison, T. S., Henz, S. R., Pape, U. J., Demar, M., Vingron, M., Schölkopf, B., Weigel, D., and Lohmann, J. U. (2005)Agene expression map of Arabidopsis thaliana development. Nat. Genet. 37, 501-506 (Pubitemid 40617278)
38. Pickel, B., Pfannstiel, J., Steudle, A., Lehmann, A., Gerken, U., Pleiss, J., and Schaller, A. (2012) A model of dirigent proteins derived from structural and functional similarities with allene oxide cyclase and lipocalins. FEBS J. 279, 1980-1993
39. Kim, K.-W., Moinuddin, S. G. A., Costa, M. A., Davin, L. B., and Lewis, N. G. (2010) in Joint Annual Meeting of the American Society of Pharmacognosy and the Phytochemical Society of North America, St. Petersburg Beach, FL, July 10-14, 2010, American Society of Pharmacognosy and Phytochemical Society of North America