Seven conformers of neutral dopamine revealed in the gas phase

Journal of Physical Chemistry Letters

Volumn 4, Issue 3, 2013, Pages 486-490

  Cabezas, Carlos ^a   Peña, Isabel ^a   López, Juan C ^a   Alonso, José L ^a  

^a UNIVERSITY OF VALLADOLID   (Spain)

Author keywords

catecholamines; conformational analysis; laser ablation; microwave spectroscopy; nuclear quadrupole coupling interactions

Indexed keywords

ABLATION; AMINES; LASER ABLATION; MICROWAVE SPECTROSCOPY; NEUROPHYSIOLOGY;

AMINO GROUP; CATECHOLAMINES; CONFORMATIONAL ANALYSIS; FOURIER TRANSFORM MICROWAVE SPECTROSCOPY; GASPHASE; NUCLEAR QUADRUPOLE COUPLINGS; PI INTERACTIONS; ROTATIONAL SPECTRA;

SPECTRUM ANALYSIS;

EID: 84873480418     PISSN: None     EISSN: 19487185     Source Type: Journal    
DOI: 10.1021/jz302135h     Document Type: Article

References (30)

1. Siegel, G. J. Basic Neurochemistry: Molecular, Cellular and Medical Aspects; Elsevier-Academic Press: London, 2006.
2. Webster, R. A. Neurotransmitters, Drugs and the Brain Function; Wiley: New York, 2001.
3. Grace, A. A. Neuropsychopharmacology-The Fifth Generation of Progress; Williams & Wilkins: New York, 2002.
4. Snoek, L. C.; Van Mourik, T.; Simons, J. P. Neurotransmitters in the Gas Phase: A Computational and Spectroscopic Study of Noradrenaline Mol. Phys. 2003, 101, 1239-1248
5. Çarçabal, P.; Snoek, L. C.; Van Mourik, T. A Computational and Spectroscopic Study of the Gas-Phase Conformers of Adrenaline Mol. Phys. 2005, 103, 1633-1639 (Pubitemid 41657176)
6. López, J. C.; Cortijo, V.; Blanco, S.; Alonso, J. L. Conformational Study of 2-Phenylethylamine by Molecular-Beam Fourier Transform Microwave Spectroscopy Phys. Chem. Chem. Phys. 2007, 9, 4521-4527
7. LeGreve, T. A.; Baquero, E.; Zwier, T. S. Infrared and Ultraviolet Spectral Signatures and Conformational Preferences of Jet-Cooled Serotonin J. Am. Chem. Soc. 2007, 129, 4028-4037, and references therein
8. Alonso, J. L.; Sanz, M. E.; López, J. C.; Cortijo, V. Conformational Behavior of Norephedrine, Ephedrine, and Pseudoephedrine J. Am. Chem. Soc. 2009, 131, 4320-4326
9. Mitsuda, H.; Miyazaki, M.; Nielsen, I. B.; ÇarcÌ §abal, P.; Dedonder, C.; Jouvet, C.; Ishiuchi, S.; Fujii, M. Evidence for Catechol Ring-Induced Conformational Restriction in Neurotransmitters J. Phys. Chem. Lett. 2010, 1, 1130-1133, and references therein
10. Ishiuchi, S.; Asakawa, T.; Mitsuda, H.; Miyazaki, M.; Chakraborty, S.; Fuvii, M. Gas-Phase Spectroscopy of Synephrine by Laser Desorption Supersonic Jet Technique J. Phys Chem. A 2011, 115, 10363-10369
11. Cabezas, C.; Varela, M.; Peña, I.; López, J. C.; Alonso, J. L. The Microwave Spectrum of Neurotransmitter Serotonin Phys. Chem. Chem. Phys. 2012, 14, 13618-13623, and references therein
12. Bergin, R.; Carlström, D. The Structure of the Catecholamines II. The Crystal Structure of Dopamine Hydrochloride Acta Crystallogr., Sect. B 1968, 24, 1506-1510
13. Giesecke, J. Refinement of The Structure of Dopamine Hydrochloride Acta Crystallogr., Sect. B 1980, 36, 178-181
14. Buustard, T. M.; Egan, R. S. The Conformation of Dopamine Hydrocloride Tetrahedron 1971, 27, 4457-4469
15. Solmajer, P.; Kocjan, D.; Solmajer, T. Conformational Study of Catecholamines in Solution Z. Naturforsch., C: Biosci. 1983, 38, 758-762
16. Lagutschenkov, A.; Langer, J.; Berden, G.; Oomens, J.; Dopfer, O. Infrared Spectra of Protonated Neurotransmitters: Dopamine Phys. Chem. Chem. Phys. 2011, 13, 2815-2823
17. Alonso, J. L.; Peña, I.; López, J. C.; Vaquero, V. Rotational Spectral Signatures of Four Tautomers of Guanine Angew. Chem., Int. Ed. 2009, 48, 6141-6143
18. Cabezas, C.; Varela, M.; Peña, I.; Mata, S.; López, J. C.; Alonso, J. L. The Conformational Locking of Asparagine Chem. Commun. 2012, 48, 5934-5936, and references therein
19. Peña, I.; Daly, A. M.; Cabezas, C.; Mata, S.; Bermúdez, C.; Niño, A.; López, J. C.; Grabow, J.-U.; Alonso, J. L. Disentangling the Puzzle of Hydrogen Bonding in Vitamin C J. Phys. Chem. Lett. 2013, 4, 65-69
20. Urban, J. J.; Cronin, C. W.; Roberts, R. R.; Famini, G. R. Conformational Preferences of 2-Phenethylamines. A Computational Study of Substituent and Solvent Effects on the Intramolecular Amine-Aryl Interactions in Charged and Neutral 2-Phenethylamines J. Am. Chem. Soc. 1997, 119, 12292-12299 (Pubitemid 28078718)
21. Fausto, R.; Ribeiro, M. J. S.; Pedroso de Lima, J. J. A Molecular Orbital Study on the Conformational Properties of Dopamine [1,2-Benzenediol-4(2- Aminoethyl)] and Dopamine Cation J. Mol. Struct. 1999, 484, 181-196 (Pubitemid 29343983)
22. Park, S. K.; Lee, N. S.; Lee, S. H. Vibrational Analysis of Dopamine Neutral Base Based on Density Functional Force Field Bull. Korean Chem. Soc. 2000, 21, 959-968
23. Pickett, H. M. The Fitting and Prediction of Vibration-Rotation Spectra with Spin Interactions J. Mol. Spectrosc. 1991, 148, 371-377
24. Watson, J. K. G. In Vibrational Spectra and Structure; Durig, J. R., Ed., Elsevier: Amsterdam, The Netherlands, 1977; Vol. 6, pp 1-89.
25. Gordy, W.; Cook, R. L. In Microwave Molecular Spectra, 3 rd ed.; Techniques of Chemistry; Weissberger, A., Ed.; John Wiley & Sons Inc.: New York, 1984; Vol. XVIII.
26. Blanco, S.; Lesarri, A.; López, J. C.; Alonso, J. L. The Gas Phase Structure of Alanine J. Am. Chem. Soc. 2004, 126, 11675-11683
27. Melandri, S.; Maris, A. Intramolecular Hydrogen Bonds and Conformational Properties of Biogenic Amines: A Free-Jet Microwave Study of Tyramine Phys. Chem. Chem. Phys. 2004, 6, 2863-2866
28. Van Mourik, T. The Shape of Neurotransmitters in the Gas Phase: A Theoretical Study of Adrenaline, Pseudoadrenaline, and Hydrated Adrenaline Phys. Chem. Chem. Phys. 2004, 6, 2827-2837
29. Frisch, M. J.; Gaussian03, revision B.04; Gaussian, Inc: Pittsburgh, PA, 2003.
30. Alonso, J. L.; Pérez, C.; Sanz, M. E.; López, J. C.; Blanco, S. Seven Conformers of l -Threonine in the Gas Phase: A LA-MB-FTMW Study Phys. Chem. Chem. Phys. 2009, 11, 617-627, and references therein