title: The binding of triazine herbicides to the photosynthetic reaction center of Rhodopseudomonas viridis. Energy minimization studies.
abstract: The binding of six herbicides of the triazine family to the photosynthetic reaction center of Rhodopseudomonas viridis was investigated with energy-minimization techniques, in order to correlate experimental with calculated data. The inhibitors were modeled in the active site according to the X-ray structure analysis of the complex formed between the triazine terbutryn (2-ethylamino-4-t-butylamino-6-methylthio-s-triazine) and the reaction center of R. viridis [Michel, H., Epp. O. & Deisenhofer, J. (1986) EMBO J. 5, 2445-2451]. 40 different energy minimizations were carried out with varying cutoff radii, partial charges on inhibitor atoms and dielectric constants, i.e. 10 different combinations of these were tested. The impact of these parameters on the calculated binding and interaction energy was either examined for all protein/triazine complexes or, in the case of the dielectric constant, a smaller sample was used. The calculated energies are dominated by van der Waals interactions, which change by up to 20% when extending the cutoff radius from 0.8 nm to 1.5 nm. The use of uniform or distance-dependent dielectric constant or partial charges on the inhibitor atoms does not severely influence the resulting structures, but shows a great impact on the calculated energies. In the two groups of triazines, each containing three inhibitors with methoxy or methylthio substituents, correlations of biological and calculated data were found quite often, but only once with all six triazines. The energy-minimized structures were compared and analysed. A third hydrogen bond, not seen in the X-ray analysis of the reaction center/tertubryn complex, was found between the t-butylamino moiety of terbutryn (and equivalent moieties in the other triazines) and the carbonyl oxygen of TyrL222.
authors.affiliation: Schering AG, Berlin, Federal Republic of Germany.
authors.forename: U
authors.initials: U
authors.lastname: Egner
authors.forename: G A
authors.initials: GA
authors.lastname: Hoyer
authors.forename: W
authors.initials: W
authors.lastname: Saenger
mesh_terms: D055598:Chemical Phenomena; D002627:Chemistry, Physical; D003460:Crystallization; D004563:Electrochemistry; D006540:Herbicides / Q000737:chemistry / Q000378:metabolism*; D006860:Hydrogen Bonding; D015394:Molecular Structure; D045322:Photosynthetic Reaction Center Complex Proteins / Q000378:metabolism*; D012241:Rhodopseudomonas / Q000378:metabolism*; D013816:Thermodynamics; D014227:Triazines; D014961:X-Ray Diffraction
chemical_list: D006540:Herbicides; D045322:Photosynthetic Reaction Center Complex Proteins; D014227:Triazines