title: Lipase-catalyzed synthesis and characterization of 1-butanoyl-2-palmitoyl phosphatidylcholine, a potential lipidic prodrug of butyric acid.
abstract: 1-Butanoyl-2-palmitoyl phosphatidylcholine was synthesized from dipalmitoylphosphatidylcholine (DPPC) and butyric acid using a lipase catalyzed transesterification in toluene at controlled water activity. A high fatty acid concentration and low water activity were essential for the enzymatic synthesis. The transesterification resulted in 97.3% incorporation of butyric acid in the sn-1 position with negligible incorporation in the sn-2-position. In mixtures with water, a liquid crystalline phase was formed in equilibrium with a micellar phase. The prepared phospholipid derivative could find applications as a lipidic anticancer prodrug of butyric acid.
authors.affiliation: Dept. of Biotechnology, Lund University, Sweden.
authors.forename: Shiva Shanker
authors.initials: SS
authors.lastname: Kaki
authors.forename: Patrick
authors.initials: P
authors.lastname: Adlercreutz
mesh_terms: D015060:1,2-Dipalmitoylphosphatidylcholine / Q000737:chemistry / Q000378:metabolism; D055162:Biocatalysis; D020148:Butyric Acid / Q000737:chemistry / Q000378:metabolism*; D004800:Enzymes, Immobilized / Q000737:chemistry / Q000378:metabolism; D008049:Lipase / Q000378:metabolism*; D010713:Phosphatidylcholines / Q000096:biosynthesis* / Q000737:chemistry; D011355:Prodrugs / Q000737:chemistry / Q000378:metabolism*
chemical_list: C559996:1-butanoyl-2-palmitoyl phosphatidylcholine; D004800:Enzymes, Immobilized; D010713:Phosphatidylcholines; D011355:Prodrugs; D020148:Butyric Acid; D015060:1,2-Dipalmitoylphosphatidylcholine; D008049:Lipase