Synthesis of 6-phosphatidyl-L-ascorbic acid by phospholipase D.
Phospholipase D (EC 3.1.4.4) of Streptomyces species was found to catalyze transphosphatidylation to L-ascorbic acid from phosphatidylcholine (PC) in a biphasic reaction system. The product was identified as 1,2-diacyl-sn-glycero-3-phospho-6'-L-ascorbic acid (PA-AsA) by mass spectrometry and nuclear magnetic resonance spectroscopy. The optimal pH of transphosphatidylation was 4.5 and the rate of PA-AsA formation increased as concentrations of L-ascorbic acid increased. The conversion of PC to PA-AsA was greater than 80%. PA-AsA was found to be more resistant to hydrolysis by phospholipase D than was PC.
Nagao
A
A
National Food Research Institute, Ministry of Agriculture, Forestry and Fisheries, Ibaraki, Japan.
Ishida
N
N
Terao
J
J
D001205:Ascorbic Acid / Q000031:analogs & derivatives* / Q000096:biosynthesis / Q000737:chemistry; D020404:Glycerophospholipids; D006863:Hydrogen-Ion Concentration; D007700:Kinetics; D009682:Magnetic Resonance Spectroscopy / Q000379:methods; D010712:Phosphatidic Acids / Q000096:biosynthesis* / Q000737:chemistry; D010739:Phospholipase D / Q000378:metabolism*; D016339:Spectrometry, Mass, Fast Atom Bombardment; D013302:Streptomyces / Q000201:enzymology; D013997:Time Factors
D020404:Glycerophospholipids; D010712:Phosphatidic Acids; C066251:6-phosphatidylascorbic acid; D010739:Phospholipase D; D001205:Ascorbic Acid