Synthesis and characterization of a dianionic carbohydrate-based phospholipid.

ABSTRACT

A novel carbohydrate-based phospholipid containing a phosphatidic acid head group, bis-(2,3-lauroyl)-1-methoxy-5-ribo-phosphatidic acid (DLRPA), was synthesized and characterized by 1H NMR, 13C NMR, and 31P NMR. This molecule is an analog of dilauroyl phosphatidic acid (DLPA). The T(m) of DLRPA decreases with increasing pH in a similar pattern to DLPA, as determined by MDSC. From this thermotropic behavior, the apparent pK(a)s of DLRPA are estimated to be 4 and 8.