| | 1 | Author
| Alfred Gieren, Michail Kokkinidis | Requires cookie* | | | Title
| Structure Investigations o f Agonists o f the Natural Neurotransmitter Acetylcholine II [1| X-ray Structure Analysis o f Trimethyl(4-oxopentyl)ammonium-chloride  | | | | Abstract
| The crystal structure of Trimethyl(4-oxopentyl)ammonium-chloride ([(C H 3) 3 N —(CH^aCOCHjJCl-) (1) was determined by an X-ray structure analysis. 1 crystallizes in the orthorhombic space group P21 21 21 with a = 10.440 (3), b = 14.600 (9), c = 6.804 (9) A and with four formula units per unit cell. The structure was solved by a Patterson and a successive Fourier synthesis. The least squares refinement yielded an R-value o f 0.064 for 1077 observed reflections. The cation o f 1 is derived from acetylcholine by replacement o f the ester oxygen with a CH2 group. It shows a potent nicotinic activity and a significant difference in conformation as compared with acetylcholine. In the crystal structure the anions are oriented stereospecifically with respect to the tetrahedron of the quaternary ammonium group. The geometry o f two triangles formed by the quaternary nitrogen atom, the oxygen atom o f the carbonyl group, and by either o f the two anions nearest to the quaternary ammonium group is characteristic for the nicotinic activity o f 1. | | | |
Reference
| Z. Naturforsch. 37c, 282 (1982); received December 231981 | | | |
Published
| 1982 | | | |
Keywords
| X-ray, Neurotransmitter, Cation-Anion Interactions, Structure-Activity Relationships | | | |
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| default:Reihe_C/37/ZNC-1982-37c-0282.pdf | | | | Identifier
| ZNC-1982-37c-0282 | | | | Volume
| 37 | |
| 2 | Author
| Alfred Gieren, Michail Kokkinidis | Requires cookie* | | | Title
| Structure Investigations of Agonists of the Natural Neurotransmitter Acetylcholine, III [1 ] X-Ray Structure Analysis of (2-Ethoxyethyl)trimethyl- ammonium Chloride | | | | Abstract
| To elucidate the structure-activity correlations we have performed an X-ray structure analysis of the title compound (1), which is a muscarinic agonist o f the natural neurotransmitter acetyl choline. 1 crystallizes in the monoclinic space group P 2)/n with 2 molecules per asymmetric unit. Lattice parameters are: a = 10.375(6), 6 = 12.468(5), c = 15.274(17) A; /?= 95.32(7)°. The structure was solved by direct methods and refined to an /?-value o f 0.14 for 1828 observed reflections. Both cations in the asymmetric unit are disordered. In the crystal structure at least four conformations of the cation occur, indicating a pronounced conformational flexibility o f the neurotransmitter cation. The anions are arranged stereospecifically with respect to the quaternary trimethylammonio methyl group. The geometry of triangles which are defined by a nitrogen o f the quaternary ammonium group and an ether oxygen on one hand and an anion occupying a specific type of tetrahedral faces of a (CH3)3N +-C H 2 group on the other hand, is characteristic for muscarinic agonists if they contain an ether or ester oxygen in the analogous position to the ester oxygen of acetylcholine. | | | |
Reference
| Z. Naturforsch. 37c, 977 (1982); received May 19/June 30 1982 | | | |
Published
| 1982 | | | |
Keywords
| X-Ray Structure Analysis, Neurotransmitter, Conformational Flexibility, Structure-Activity Correlation | | | |
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| default:Reihe_C/37/ZNC-1982-37c-0977.pdf | | | | Identifier
| ZNC-1982-37c-0977 | | | | Volume
| 37 | |
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