In all domains of life, homochiral lipid bilayers serve as the core structure of cell membranes. While membrane structure and permeability are largely due to the amphiphilic nature of the phospholipid bilayer, stereochemistry plays an important and often overlooked role in these functions. Membranes of the archaeal kingdom contain phospholipids of the opposite chirality to those of the bacterial and eukaryotic kingdoms. Specifically, archaeal phospholipids have glycerol-1-phosphate (G1P) in the L configuration, whereas bacterial and eukaryotic phospholipids contain glycerol-3-phosphate (G3P) in the D configuration. In order to study the differences in membrane physical properties resulting from this stereochemical difference, we have built and simulated bilayers containing G1P palmitoyl oleoyl phosphatidyl choline (POPC) and its enantiomer G3P-POPC. Simulations of 1:0, 1:1, and 0:1 G1P-POPC:G3P-POPC have indicated that structural properties are overall very similar across these membranes; however, simulations that include an aromatic amino acid (phenylalanine) show a difference in partitioning between the G1P and G3P membranes. Additionally, simulations of G1P- and G3P-POPC with cholesterol suggest chiral differences in cholesterol induced lipid packing.
Kimelheim et al. (Sun,) studied this question.