Conformation and hydration of acetylcholine

Kim, Young Ju; Kim, Shi Choon; Kang, Young Kee

doi:10.1016/0022-2860(92)80019-e

Cited by 10 publications

(3 citation statements)

References 30 publications

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“…The five ACh + conformers (tg * g, tgg, ttg, tgt, and ttt) are in the low-level group (Figure 3a-e), and the other two conformers (ctg and ctt) are in the high-level group (Figure 3f,g). Other computational studies [20,23,39,40] also conclude the stability of the five low-level conformers. It is important to note that our results support the experiments that observed ACh + (tg * g), (tgg), and (ttg) in their stable states [29,41,42].…”

Section: Thermochemistry Calculationsmentioning

confidence: 88%

“…Therefore, the backbone and the tail must curl up in order to shorten the head-tail distance. Such curling behavior does not only exist in gas phase but also in solvent [18,20,23,27]. The gauche conformation at D2 and D3 meets the condition, particularly at D3, where the head-tail distance is the shortest.…”

Section: R1mentioning

confidence: 91%

“…The dependency is stronger when the reaction involves an enzyme as a catalyst [14,15]. In the ACh + case, at least three conformers have been investigated to understand their stability and the interconversion among the conformers and to explore the fluorination and solvent effects on each of them [16][17][18][19][20][21][22][23][24][25][26][27]. However, to the best of our knowledge, studies of ACh + conformers remain limited to its stability as an individual molecule.…”

Section: Introductionmentioning

confidence: 99%

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A Density-Functional Study of the Conformational Preference of Acetylcholine in the Neutral Hydrolysis

et al. 2020

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Acetylcholine, which is associated with Alzheimer’s disease, is widely known to have conformers. The preference of each conformer to undergo neutral hydrolysis is yet to be considered. In this study, we employed density-functional calculations to build the conformers and investigated their preference in one-step neutral hydrolysis. The results showed the preference in ten possible hydrolysis pathways involving seven acetylcholine conformers (reactant), four transition state structures, and two choline conformers (product). Three out of the seven acetylcholine conformers predicted from the results confirmed experimental findings on the conformers stability. We suggested that two out of ten possible pathways were observed in the experimental results based on agreement in reaction energy. Eventually, this study will emphasize the importance of considering acetylcholine conformers in its hydrolysis study.

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Section: Thermochemistry Calculationsmentioning

confidence: 88%

Section: R1mentioning

confidence: 91%

Section: Introductionmentioning

confidence: 99%

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A Density-Functional Study of the Conformational Preference of Acetylcholine in the Neutral Hydrolysis

et al. 2020

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ChemInform Abstract: Conformation and Hydration of Acetylcholine

Kim

Kang

1992

ChemInform

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A DFT study of determination of the reactive sites of the acetylcholine and its agonists: In the gas phase and dielectric medium

Serdaroğlu

2011

Int J of Quantum Chemistry

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The reactive behavior of acetylcholine and its agonist molecules have been investigated using B3LYP hybrid density functional method at the 6-311þþG** basis set level, in the gas phase and aqueous phase. The calculations have been performed to obtain optimized geometries, relative reactivities, net atomic charges, HOMO, and LUMO energies. The solvent effect has been analyzed by using the continuum model (IPCM) and, the obtained results have shown that the all molecules have been stabilized more by solvent dielectric constant. For Ach and its analogues, it has been very well known that esteratic site and quaternary ammonium group which have reflected the difference in biological activity have been the two of the most important active site for interactions between molecule and its receptor. The structures of these analogues have provided an essential foundation for subsequent structureactivity analysis of ligand binding at acetylcholine receptors, neuronal uptake inhibitors and transporters. Molecular modeling predictions will be important initial steps toward the development of novel pharmaceuticals in the fight acetylcholine-related neurological disorders. This work is therefore expected to facilitate the design and development of new biologically active Ach analogues to treat Ach-related neurological disorders and, specially is used to qualitative understanding of the reactivity and related properties and, so on can be used to a preselection of new ligands which at the moment is taken essentially from empirical knowledge. V

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Conformation and hydration of acetylcholine

Cited by 10 publications

References 30 publications

A Density-Functional Study of the Conformational Preference of Acetylcholine in the Neutral Hydrolysis

A Density-Functional Study of the Conformational Preference of Acetylcholine in the Neutral Hydrolysis

ChemInform Abstract: Conformation and Hydration of Acetylcholine

A DFT study of determination of the reactive sites of the acetylcholine and its agonists: In the gas phase and dielectric medium

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