How Different are the Crystal Structures of Chiral and Racemic Diacylphosphatidylethanolamines?

Both chiral and racemic phosphatidylethanolamines are known to crystallize in a similar polymorphic form with nearly the same lamellar spacing; yet published lamellar X-ray diffraction intensity data for those materials do not agree with one another, even though the peak positions in Patterson maps are nearly the same. Translational structural searches based on the crystal structure of the racemic compound also lead to similar packing models with both data sets, although the agreement between model and observed data is poor for the chiral compound. A separate analysis of L-DMPE based on lamellar electron diffraction data again leads to a similar lamellar structure with a better agreement between calculated and observed structure factors. The major difference seen for enantiomeric vs. racemic compounds is that, for the racemic lipid, the lateral unit cell spacings are about 3% larger than the chiral form, perhaps indicating a more stable hydrogen bonding network, in agreement with the higher melting point of the racemic compound. Attempts to explain this difference with other head group conformations, however, have not yet produced an improved structural model.