The structure of the catecholamines. II. The crystal structure of dopamine hydrochloride

Bergin, R.; Carlström, D.

doi:10.1107/s0567740868004553

Cited by 75 publications

(34 citation statements)

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“…Single crystal X-ray structure determination shows DA in a trans (fully extended, antiperiplanar) conformation (see Figure 5). 727 Although torsion angles (7, see Figure 5, iv) will not be employed in this discussion, they more completely define conformation. values for several DA receptor agonists, the reader is referred to more detailed articles and review^.…”

Section: B Conformational Requirementsmentioning

confidence: 99%

Dopamine receptors: Functions, subtypes and emerging concepts

Kaiser¹,

Jain²

1985

Medicinal Research Reviews

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Section: B Conformational Requirementsmentioning

confidence: 99%

Dopamine receptors: Functions, subtypes and emerging concepts

Kaiser¹,

Jain²

1985

Medicinal Research Reviews

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“…6,9 In contrast, the analysis of the crystal structure and IR spectra of neutral dopamine in the condensed phase yields a trans conformation, which is rationalized by the stronger stabilization through solvation when compared to the gauche conformation. 10 These studies demonstrate that solvation has a strong influence on the preferred conformation of dopamine(H + ). The conformational flexibility due to rotations about the C-N and the two C-C bonds of the ethylamine side chain of protonated dopamine is expected to be an important factor for molecular recognition phenomena in drug-receptor interactions.…”

Section: Introductionmentioning

confidence: 98%

Infrared spectra of protonated neurotransmitters: dopamine

Lagutschenkov

Langer

Berden

et al. 2011

Phys. Chem. Chem. Phys.

108

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The infrared (IR) spectrum of the isolated protonated neurotransmitter dopamine was recorded in the fingerprint range (570-1880 cm À1) by means of IR multiple photon dissociation (IRMPD) spectroscopy. The spectrum was obtained in a Fourier transform ion cyclotron resonance mass spectrometer equipped with an electrospray ionization source, which was coupled to a free electron laser (FEL). The spectroscopic studies are complemented by quantum chemical calculations at the B3LYP and MP2 levels of theory using the cc-pVDZ basis set. Several low-energy isomers with protonation occurring at the amino group are predicted in the energy range 0-50 kJ mol À1. Good agreement between the measured IRMPD spectrum and the calculated linear absorption spectra is observed for the two gauche conformers lowest in energy (DE) and free energy (DG) at both levels of theory, denoted gÀ1 and g+1. Minor contributions of higher lying gauche isomers cannot be ruled out spectroscopically but their calculated energies suggest only minor population in the sampled ion cloud. In all these gauche structures, one of the three protons of the ammonium group is pointing toward the catechol subunit, thereby maximizing the intramolecular NH-p interaction of the positive charge with the aromatic ring. In total, 16 distinct vibrational bands are observed in the IRMPD spectrum and assigned to individual normal modes of the energetically most stable gÀ1 conformer, with deviations of less than 24 cm À1 (average 11 cm À1) between measured and calculated frequencies. Comparison with neutral dopamine reveals the effects of protonation on the geometric and electronic structure.

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“…[9][10][11][12] Dopamine is synthesised from L-dihydroxyphenylalanine (L-DOPA) in neurons and in cells in the adrenal glands, but, unlike L-DOPA, dopamine is unable to cross the blood-brain barrier, in spite of its structural similarity with L-DOPA. 13 Since the first elucidation of the crystal structure of dopamine in 1968, 14 experimental and theoretical studies have been performed in order to understand how dopamine interacts with dopaminergic receptors both in terms of the conformation the dopamine molecule adopts and the interactions it forms. [15][16][17][18][19] The conformational forms of dopamine have also been studied by nuclear magnetic resonance (NMR) 20,21 across the pH range 2-11.5 and predicted by theoretical calculations [22][23][24] for both its neutral and protonated forms in the gas phase and also in aqueous solution.…”

Section: Introductionmentioning

confidence: 99%

Conformation and interactions of dopamine hydrochloride in solution

Callear

Johnston

McLain

et al. 2015

The Journal of Chemical Physics

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The aqueous solution of dopamine hydrochloride has been investigated using neutron and X-ray total scattering data together with Monte-Carlo based modelling using Empirical Potential Structure Refinement. The conformation of the protonated dopamine molecule is presented and the results compared to the conformations found in crystal structures, dopamine-complexed protein crystal structures and predicted from theoretical calculations and pharmacophoric models. It is found that protonated dopamine adopts a range of conformations in solution, highlighting the low rotational energy barrier between different conformations, with the preferred conformation being trans-perpendicular. The interactions between each of the species present (protonated dopamine molecules, water molecules, and chloride anions) have been determined and are discussed with reference to interactions observed in similar systems both in the liquid and crystalline state, and predicted from theoretical calculations. The expected strong hydrogen bonds between the strong hydrogen bond donors and acceptors are observed, together with evidence of weaker CH hydrogen bonds and π interactions also playing a significant role in determining the arrangement of adjacent molecules.

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The structure of the catecholamines. II. The crystal structure of dopamine hydrochloride

Cited by 75 publications

References 1 publication

Dopamine receptors: Functions, subtypes and emerging concepts

Dopamine receptors: Functions, subtypes and emerging concepts

Infrared spectra of protonated neurotransmitters: dopamine

Conformation and interactions of dopamine hydrochloride in solution

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