title: Molecular modelling studies on the binding of phenylurea inhibitors to the D 1 protein of photosystem II.
abstract: A hypothetical molecular model of part of the D 1 protein of photosystem II, based on the analogous portion of the L subunit of the Rhodopseudomonas viridis reaction centre, has been used to study the binding of an extended hydrophobic phenylurea inhibitor (N,N-dimethyl-carbamoyl)4-amino-4'-chloro-trans-stilbene) (I) to the QB site. The inhibitor was fitted by eye into a cleft in the site, and a limited part of the inhibitor/D 1 complex was energy minimized. The gross orientation of the inhibitor placed the dimethylurea moiety towards the predicted binding domain of the plastoquinone head group, and the stilbene moiety directed along the quinone isoprenoid side chain binding domain, suggesting a similar pathway of approach of the two molecules from the membrane into the binding site. Binding interactions of the inhibitor included hydrogen bonds to the side chain hydroxyl of ser 264 and the peptide carbonyl group of ala 251, with the side chain hydroxyl of ser 268 as an alternative ligand. Numerous hydrophobic contacts were also possible. Although phenylureas do not bind to reaction centres of Rp. viridis, many of the binding interactions to D 1 could also be detected in Rp. viridis. However, the beta-CH2, and delta-CO2- groups of glu 212 in Rp. viridis are located in the corresponding region of D 1 occupied by the dimethylurea moiety of the inhibitor in our model of its binding to D 1. This may explain why diuron (DCMU) does not bind to Rp. viridis reaction centres.
authors.affiliation: Department of Biochemistry, Royal Holloway and Bedford New College, Egham, Surrey, U.K.
authors.forename: J
authors.initials: J
authors.lastname: Bowyer
authors.forename: M
authors.initials: M
authors.lastname: Hilton
authors.forename: J
authors.initials: J
authors.lastname: Whitelegge
authors.forename: P
authors.initials: P
authors.lastname: Jewess
authors.forename: P
authors.initials: P
authors.lastname: Camilleri
authors.forename: A
authors.initials: A
authors.lastname: Crofts
authors.forename: H
authors.initials: H
authors.lastname: Robinson
mesh_terms: D000595:Amino Acid Sequence; D001665:Binding Sites; D002734:Chlorophyll / Q000037:antagonists & inhibitors / Q000378:metabolism*; D000458:Cyanobacteria / Q000378:metabolism; D045342:Light-Harvesting Protein Complexes; D046911:Macromolecular Substances; D008958:Models, Molecular; D008969:Molecular Sequence Data; D010671:Phenylurea Compounds / Q000378:metabolism*; D045322:Photosynthetic Reaction Center Complex Proteins; D045332:Photosystem II Protein Complex; D010940:Plant Proteins / Q000037:antagonists & inhibitors / Q000378:metabolism*; D010944:Plants / Q000378:metabolism*; D011485:Protein Binding; D012241:Rhodopseudomonas / Q000378:metabolism*; D013267:Stilbenes / Q000037:antagonists & inhibitors / Q000378:metabolism*
chemical_list: D045342:Light-Harvesting Protein Complexes; D046911:Macromolecular Substances; D010671:Phenylurea Compounds; D045322:Photosynthetic Reaction Center Complex Proteins; D045332:Photosystem II Protein Complex; D010940:Plant Proteins; D013267:Stilbenes; C065243:(N,N-dimethylcarbamoyl)-4-amino-4'-chlorostilbene; D002734:Chlorophyll