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Deuterium solid-state nuclear magnetic resonance studies of methyl group dynamics in bacteriorhodopsin and retinal model compounds: Evidence for a 6-s-trans chromophore in the protein

Deuterium solid-state nuclear magnetic resonance studies of methyl group dynamics in bacteriorhodopsin and retinal model compounds: Evidence for a 6-s-trans chromophore in the protein

Biochemistry 33(11): 3280-3286

ISSN/ISBN: 0006-2960

PMID: 8136363

DOI: 10.1021/bi00177a019

Solid-state deuterium NMR spectroscopy is used to examine the dynamic behavior of 18-CD-3 methyl groups in microcrystalline 6-s-cis-retinoic acid (triclinic) and 6-s-trans-retinoic acid (monoclinic) model compounds, as well as in the membrane protein bacteriorhodopsin (bR), regenerated with CD-3-labeled retinal. Temperature dependent quadrupolar echo line shapes and T-1 anisotropy measurements were used to characterize activation energies for 3-fold hopping motion of the methyl groups. These data provide supporting evidence that the conformation of the retinal chromophore in bR is 6-s-trans. The 6-s-cis conformer is characterized by strong eclipsing interactions between the 8-C proton and the 18-C methyl group protons; the 18-CD-3 group shows an activation energy barrier for methyl 3-fold hopping of 14.5 +- 1 kJ/mol. In contrast, the 18-CD-3 group in the 6-s-trans isomer shows a considerably lower activation energy barrier of 5 +- 1 kJ/mol. In bR, it is possible to obtain an approximate activation energy of 9 kJ/mol. This data is inconsistent with a 6-s-cis conformer but is consistent with the existence of a 6-s-trans-retinal Schiff base in bR with some interaction with the protein matrix. These results suggest that methyl rotor motions can be used to probe the van der Waals contact between a ligand and a protein binding pocket. The 6-s-trans conformer of the (16,17-(CD-3)-2)retinal in frozen hexane exhibits a major kinetic component with an activation energy barrier of 14 +- 2 kJ/mol. For the (16,17-(CD-3)-2)retinal in bR, line shapes indicate an activation energy of 13 +- 2 kJ/mol within error of that for the 6-s-trans model compound. Our results illustrate the use of deuterium NMR techniques to probe local group motions in a relatively large membrane protein like bR and they illustrate a novel solution to a structural problem by measuring molecular dynamics of pertinent functional groups.

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