GluR2 ligand-binding core complexes: importance of the isoxazolol moiety and 5-substituent for the binding mode of AMPA-type agonists.

X-ray structures of the GluR2 ligand-binding core in complex with (S)-Des-Me-AMPA and in the presence and absence of zinc ions have been determined. (S)-Des-Me-AMPA, which is devoid of a substituent in the 5-position of the isoxazolol ring, only has limited interactions with the partly hydrophobic pocket of the ligand-binding site, and adopts an AMPA-like binding mode. The structures, in comparison with other agonist complex structures, disclose the relative importance of the isoxazolol ring and of the substituent in the 5-position for the mode of binding. A relationship appears to exist between the extent of interaction of the ligand with the hydrophobic pocket and the affinity of the ligand.

Alkyl ether and enol ether analogs of (Z)-5-decenyl acetate, a pheromone component of the turnip moth,Agrotis segetum: probing a proposed bioactive conformation for chain-elongated analogs.

In order to test a previous conclusion that chain-elongated analogs of (Z)-5-decenyl acetate(1), a pheromone component of the turnip moth,Agrotis segetum, adopt a loop conformation of the terminal alkyl chain in the bioactive conformation, a series of alkyl ether and enol ether analogs of1 and (Z)-5-dodecenyl acetate(2) have been synthesized and tested using singlecell electrophysiology. In these analogs a methylene group in positions 7 and 9 of1 and in positions 7 and 11 in2 have been replaced by an oxygen atom in order to energetically facilitate the formation of a loop conformation in the chain-elongated analogs. The electrophysiological results in combination with molecular mechanics (MM2 and MM3) calculated conformational energies show that the activity decreases of the chain-elongated ether analogs are significantly smaller than that for2 and that these activity decreases parallel the conformational energies for a loop formation of the terminal chains in the analogs. The results support our previous conclusion that the terminal chain of chain-elongated analogs of1 adopts a loop conformation in their bioactive conformations.

Determination of the vapor pressures of moth sex pheromone components by a gas chromatographic method.

The vapor pressures of decyl acetate, five decenyl acetate isomers, (Z)-7-dodecenyl acetate, and (Z)-9-tetradecenyl acetate have been determined at three to six temperatures in the interval 25-45 °C by a gas Chromatographic method suitable for accurate measurements of the low vapor pressures of moth sex pheromone components at biologically relevant temperatures. The vapor pressure values at 30.5 °C are 3.80 Pa for decyl acetate, 4.08-5.40 Pa for the decenyl acetate isomers, 0.562 Pa for (Z)-7-dodecenyl acetate, and 0.094 Pa for (Z)-9-tetradecenyl acetate. The vapor pressures of the decenyl acetates show a small but significant dependence on the double bond position. Four of the compounds in this study, 10∶Ac,Z5-10∶Ac,Z7-12∶Ac, andZ9-14∶Ac have recently been identified as sex pheromone components of the turnip moth,Agrotis segetum. Large differences between the mole percentages of the component as found in liquid extracts of female abdominal tips and the corresponding mole percentages in the vapor phase are predicted.