期刊
JOURNAL OF BIOLOGICAL CHEMISTRY
卷 295, 期 33, 页码 11584-11601出版社
ELSEVIER
DOI: 10.1074/jbc.RA120.012444
关键词
crystallography; dimerization; docking; plant biochemistry; plant defense; dirigent protein; lignans; lignins; pterocarpans; quinone methides
资金
- Office of Biological and Environmental Research
- Department of Energy, Office of Science, Basic Energy Sciences (BES) [DE-AC02-76SF00515]
- Department of Energy Office of Biological and Environmental Research (BER)
- NIGMS, National Institutes of Health [P41GM103393]
The biochemical activities of dirigent proteins (DPs) give rise to distinct complex classes of plant phenolics. DPs apparently began to emerge during the aquatic-to-land transition, with phylogenetic analyses revealing the presence of numerous DP subfamilies in the plant kingdom. The vast majority (>95%) of DPs in these large multigene families still await discovery of their biochemical functions. Here, we elucidated the 3D structures of two pterocarpan-forming proteins with dirigent-like domains. Both proteins stereospecifically convert distinct diastereomeric chiral isoflavonoid precursors to the chiral pterocarpans, (-)- and (+)-medicarpin, respectively. Their 3D structures enabled comparisons with stereoselective lignan- and aromatic terpenoid-forming DP orthologs. Each protein provides entry into diverse plant natural products classes, and our experiments suggest a common biochemical mechanism in binding and stabilizing distinct plant phenol-derived mono- and bis-quinone methide intermediates during different C-C and C-O bond-forming processes. These observations provide key insights into both their appearance and functional diversification of DPs during land plant evolution/adaptation. The proposed biochemical mechanisms based on our findings provide important clues to how additional physiological roles for DPs and proteins harboring dirigent-like domains can now be rationally and systematically identified.
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