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

Autor(es)

da Silva, Julio Cesar A. ^[1] ; Ducati, Lucas C. ^[1] ; Rittner, Roberto ^[1]

Afiliação do(s) autor(es)

^[1] Univ Estadual Campinas, Inst Chem, Phys Organ Chem Lab, BR-13083970 Campinas, SP - Brazil

• Tipo de documento: Artigo Científico
• Fonte: Journal of Molecular Structure; v. 1015, p. 33-40, MAY 16 2012.
• Citações Web of Science: 2

Resumo

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)

• Processo FAPESP: 05/59649-0 - Estudos de estrutura eletrônica e molecular através de métodos espectroscópicos e cálculos teóricos
• Beneficiário: Roberto Rittner Neto
• Modalidade de apoio: Auxílio à Pesquisa - Temático
• Processo FAPESP: 09/54071-0 - EMU: modernização do laboratório de RMN do IQ-UNICAMP: aquisição de um 600 MHz para experimentos em solução
• Beneficiário: Roberto Rittner Neto
• Modalidade de apoio: Auxílio à Pesquisa - Programa Equipamentos Multiusuários