A reinvestigation of the crystal structure of acetylcholine bromide

Svinning, T.; Sørum, H.

doi:10.1107/s0567740875005729

Cited by 43 publications

(30 citation statements)

References 9 publications

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“…This result is in disagreement with a series of experimental studies [7,8,19,20] in which it was observed that the s 2 dihedral is often in the gauche conformation. The reason for which the gauche conformation should be favoured was justi®ed by invoking that``ACh + can be considered a member of a class of 1,2-disubstituted ethanes in which the increased stability of the gauche conformation is the norm.…”

Section: In Vacuocontrasting

confidence: 81%

Molecular dynamics, density functional and second-order Møller-Plesset theory study of the structure and conformation of acetylcholine in vacuo and in solution

Marino

Russo

Tocci

et al. 2001

Theoretical Chemistry Accounts: Theory, Computation, and Modeli

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Molecular mechanics minimizations based on the CVFF force ®eld and molecular dynamics simulation for a time of 2.5 ns were performed to examine the conformational behaviour and the molecular motion of acetylcholine in vacuo and in aqueous solution. Five low-lying conformations, namely the TT, TG, GG, G*G and GT, were obtained from molecular mechanics computations with the GT structure as the absolute minimum. Molecular dynamics trajectories in vacuo and in water show that only four (GT, GG, G*G and TG) and three (TG, TT and GT) conformations are present in the simulation time, respectively. Density functional B3LYP and second-order Mùller± Plesset (MP2) methods were then used to study all the ®ve lowest-lying conformers of acetylcholine neurotransmitter in vacuo and in water by the polarizable continuum model approach. The B3LYP and MP2 computations show that in the gas phase all minima lie in a narrow range of energy with the G*G conformer as the most stable one. The relative minima GG, GT, TG and TT are located at 1.1 (3.3), 1.8 (4.2), 2.1 (4.5) and 4.3 (7.3) kcal/mol above the absolute one at the B3LYP (MP2) level. The preferred conformation in water is the TG. Solvation reduces the relative energy dierences between the ®ve minima in both computations.

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Section: In Vacuocontrasting

confidence: 81%

Molecular dynamics, density functional and second-order Møller-Plesset theory study of the structure and conformation of acetylcholine in vacuo and in solution

Marino

Russo

Tocci

et al. 2001

Theoretical Chemistry Accounts: Theory, Computation, and Modeli

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show abstract

“…The C-C bond within the N + -C-C-O- grouping can rotate freely, but in both the crystal and solution structures, the gauche conformation predominates over the trans conformation (40, 256). In the gauche conformation, the reduced distance of 3.3 Å between quaternary nitrogen and ether oxygen atoms increases intramolecular electrostatic stabilization, promoting that conformation.…”

Section: Pharmacologymentioning

confidence: 99%

End-Plate Acetylcholine Receptor: Structure, Mechanism, Pharmacology, and Disease

Sine

2012

Physiological Reviews

112

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The synapse is a localized neurohumoral contact between a neuron and an effector cell and may be considered the quantum of fast intercellular communication. Analogously, the postsynaptic neurotransmitter receptor may be considered the quantum of fast chemical to electrical transduction. Our understanding of postsynaptic receptors began to develop about a hundred years ago with the demonstration that electrical stimulation of the vagus nerve released acetylcholine and slowed the heart beat. During the past 50 years, advances in understanding postsynaptic receptors increased at a rapid pace, owing largely to studies of the acetylcholine receptor (AChR) at the motor endplate. The endplate AChR belongs to a large superfamily of neurotransmitter receptors, called Cys-loop receptors, and has served as an exemplar receptor for probing fundamental structures and mechanisms that underlie fast synaptic transmission in the central and peripheral nervous systems. Recent studies provide an increasingly detailed picture of the structure of the AChR and the symphony of molecular motions that underpin its remarkably fast and efficient chemoelectrical transduction.

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“…Thus, one can expect important variations in frequency, especially for the v(C=O) vibration which is not overlapped by another one. On the basis of more precise X-ray reinvestigation of the AchBr crystal structure [141], a correction of the length of (C=O) bond to 1.19 A and of (C-O) bond to 1.36 A has been made for this compound. On the basis of more precise X-ray reinvestigation of the AchBr crystal structure [141], a correction of the length of (C=O) bond to 1.19 A and of (C-O) bond to 1.36 A has been made for this compound.…”

Section: Conformation Of Acetylcholinementioning

confidence: 99%

Molecules in Physics, Chemistry, and Biology

Maruani¹

1989

Topics in Molecular Organization and Engineering

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A reinvestigation of the crystal structure of acetylcholine bromide

Cited by 43 publications

References 9 publications

Molecular dynamics, density functional and second-order Møller-Plesset theory study of the structure and conformation of acetylcholine in vacuo and in solution

Molecular dynamics, density functional and second-order Møller-Plesset theory study of the structure and conformation of acetylcholine in vacuo and in solution

End-Plate Acetylcholine Receptor: Structure, Mechanism, Pharmacology, and Disease

Molecules in Physics, Chemistry, and Biology

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