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Stereoselective Bimolecular Phenoxy Radical Coupling by an Auxiliary (Dirigent) Protein Without an Active Center
Abstract
The regio- and stereospecificity of bimolecular phenoxy radical coupling reactions, of especial importance in lignin and lignan biosynthesis, are clearly controlled in some manner in vivo; yet in vitro coupling by oxidases, such as laccases, only produce racemic products. In other words, laccases, peroxidases, and comparable oxidases are unable to control regio- or stereospecificity by themselves and thus some other agent must exist. A 78-kilodalton protein has been isolated that, in the presence of an oxidase or one electron oxidant, effects stereoselective bimolecular phenoxy radical coupling in vitro. Itself lacking a catalytically active (oxidative) center, its mechanism of action is presumed to involve capture of E -coniferyl alcohol-derived free-radical intermediates, with consequent stereoselective coupling to give (+)-pinoresinol.
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Citations
Cited by
Boerjan, W., Ralph, J., & Baucher, M. (2003) · Annual Review of Plant Biology · doi:10.1146/annurev.arplant.54.031902.134938 · Cited by 4,504
Genome-wide analysis of phenylpropanoid defence pathways.
NAOUMKINA, M. A., ZHAO, Q., GALLEGO‐GIRALDO, L., DAI, X., ZHAO, P. X., & DIXON, R. A. (2010) · Molecular Plant Pathology · doi:10.1111/j.1364-3703.2010.00648.x · Cited by 410
Touré, A., & Xueming, X. (2010) · Comprehensive Reviews in Food Science and Food Safety · doi:10.1111/j.1541-4337.2009.00105.x · Cited by 406
Enantiomeric Natural Products: Occurrence and Biogenesis
Finefield, J. M., Sherman, D. H., Kreitman, M., & Williams, R. M. (2012) · Angewandte Chemie International Edition · doi:10.1002/anie.201107204 · Cited by 299
Lignin Formation in Plants. The Dilemma of Linkage Specificity
Hatfield, R., & Vermerris, W. (2001) · Plant Physiology · doi:10.1104/pp.126.4.1351 · Cited by 284
Metadata
- Authors
- Davin, L. B., Wang, H.-B., Crowell, A. L., Bedgar, D. L., Martin, D. M., Sarkanen, S., & Lewis, N. G.
- Venue
- Science
- Published
- 1997-01-17
- Volume
- 275
- Issue
- 5298
- Pages
- 362-367
- ISSN
- 0036-8075 (ISSN-L)
- 1095-9203
- OpenAlex
- W2023343774
- Cited by
- 755
- References
- 0
- FWCI
- 6.97
- Type
- journal article
- Language
- en
- Open access
- closed
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- CoChat. (2026). Citation check: Stereoselective Bimolecular Phenoxy Radical Coupling by an Auxiliary (Dirigent) Protein Without an Active Center. https://app.cochat.ai/papers/10.1126/science.275.5298.362
- The paper
- Davin, L. B., Wang, H.-B., Crowell, A. L., Bedgar, D. L., Martin, D. M., Sarkanen, S., & Lewis, N. G. (1997). Stereoselective Bimolecular Phenoxy Radical Coupling by an Auxiliary (Dirigent) Protein Without an Active Center. Science. https://doi.org/10.1126/science.275.5298.362
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Contains information from the Semantic Scholar Academic Graph Datasets, made available under the ODC Attribution License (ODC-BY 1.0).
Semantic Scholar’s data is described in: Kinney, R., et al. (2023). The Semantic Scholar Open Data Platform. arXiv:2301.10140.
