Conformational study of galphimines A and B.
A conformational study has been performed for galphimines A and B, which differ from each other only in an acetate moiety on ring B of galphimine A. Mechanical molecular calculations showed that the predominant conformers in a Boltzman distribution are those which establish an intramolecular hydrogen bond between the hydroxyls on rings A and B, keeping a similar conformation on the rest of the molecule. The existence of these conformers was confirmed by NMR spectroscopy in (D6) DMSO solution. Furthermore, an unbound hydrogen conformation was found. These types of conformations very probably coexist in solution, for both types of galphimines A and B. Additional experiments suggest that the acetate group on galphimine A does not distort rings B and A, neither does it disturb the intramolecular hydrogen bond formation that also shows galphimine B. Finally, it does not present a steric effect on ring A to avoid any type of interaction of the functional groups on this ring with the biological receptor. The acetate group, which is responsible for the lost of activity of galphimine A very probably prevent that the hydroxyls OH4 and OH7 from interacting, either in a hydrogen bounded or free form, with the receptor, indicating the importance that these hydroxyls play in the biological activity of the molecule.
Lara-Ochoa
F
F
Instituto de Química, Universidad Nacional Autónoma de México, Circuito Exterior, Ciudad Universitaria, Coyoacán, México 04510, D.F., México. flara@servidor.unam.mx
Guillén-Torres
A
A
Espinosa-Pérez
G
G
Ortega-Hernández
A
A
D004121:Dimethyl Sulfoxide; D006860:Hydrogen Bonding; D009682:Magnetic Resonance Spectroscopy; D008958:Models, Molecular; D008968:Molecular Conformation; D012996:Solutions / Q000737:chemistry; D013696:Temperature; D014315:Triterpenes / Q000737:chemistry*; D014867:Water / Q000737:chemistry
D012996:Solutions; D014315:Triterpenes; C504560:galphimine A; D014867:Water; C084708:galphimine B; D004121:Dimethyl Sulfoxide