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Conformational analysis and electronic structure calculations of S ‐1,2‐bis(2‐dibutenoyl)glycerol and S ‐1,2‐bis(2,4‐hexadienoyl)glycerol, two analogues of 1,2‐bis(2,4‐octadecadienoyl)‐ sn ‐glycero‐3‐phosphorylcholine
Author(s) -
Faupel Peter,
Buß Volker
Publication year - 1992
Publication title -
macromolecular theory and simulations
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.37
H-Index - 56
eISSN - 1521-3919
pISSN - 1022-1344
DOI - 10.1002/mats.1992.040010505
Subject(s) - dihedral angle , cndo/2 , chemistry , crystallography , circular dichroism , computational chemistry , conformational isomerism , ab initio , molecule , hydrogen bond , organic chemistry
As a model for 1,2‐bis(2,4‐octadecadienoyl)‐ sn ‐glycero‐3‐phosphorylcholine, a doubly unsaturated membrane‐forming lipid molecule, force‐field (MMP2) calculations were performed on S ‐1,2‐bis(2‐dibutenoyl)glycerol, and CNDO/S‐calculations 2 CNDO: Complete neglect of differential overlap, a semi‐empirical quantum‐mechanical method. on the derived minimum‐energy conformations of S ‐1,2‐bis(2,4‐hexadienoyl)glycerol. The energy hypersurface especially with respect to the dihedral angles along the C(1)‐C(2) and the two CO ester bonds was explored and the rotational strength as a function of these angles was calculated. The two gauche ‐forms were found to be most stable, with a slight preference for the g − ‐form. The experimental circular dichroism data obtained for 1,2‐bis(2,4‐hexadienoyl)‐ sn ‐glycero‐3‐phosphorylcholine, the corresponding phosphorylcholine, indicate a dynamic equilibrium between two forms of opposite chirality possibly involving the g + ‐and the g − ‐forms.