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(Reference retrieved automatically from Web of Science through information on FAPESP grant and its corresponding number as mentioned in the publication by the authors.)

Conformational and stereoeletronic investigations of muscarinic agonists of acetylcholine by NMR and theoretical calculations

Full text
Author(s):
da Silva, Julio Cesar A. [1] ; Ducati, Lucas C. [1] ; Rittner, Roberto [1]
Total Authors: 3
Affiliation:
[1] Univ Estadual Campinas, Inst Chem, Phys Organ Chem Lab, BR-13083970 Campinas, SP - Brazil
Total Affiliations: 1
Document type: Journal article
Source: Journal of Molecular Structure; v. 1015, p. 33-40, MAY 16 2012.
Web of Science Citations: 2
Abstract

NMR solvent effects and theoretical calculations showed muscarinic agonists present a large stability for their near synclinal conformations, indicating the presence of significant stabilization factors. Analysis of the results clearly indicated that this stability is not determined by the dihedral around the substituted C-C ethane bond, as stated by some authors, but a consequence of the geometry adopted in order to maximize N+/O interactions in this type of molecules. It can be assumed that acetylcholine and its muscarinic agonists exhibit their biologic activity when the positively charged nitrogen and the oxygen atoms are in the same side of the molecule within an interatomic distance ranging from 3.0 to 6.0 angstrom. (C) 2012 Elsevier B.V. All rights reserved. (AU)

FAPESP's process: 05/59649-0 - Conformational equilibria studies by nuclear magnetic resonance spectroscopy, infrared spectroscopy and theoretical calculations
Grantee:Roberto Rittner Neto
Support Opportunities: Research Projects - Thematic Grants
FAPESP's process: 09/54071-0 - Modernization of the NMR Laboratory of the UNICAMP, Institute of Chemistry: acquisition of a 600-MHz spectrometer for experiments in solution
Grantee:Roberto Rittner Neto
Support Opportunities: Multi-user Equipment Program