Premium
An enzymatic method for the synthesis of mixed‐acid phosphatidylcholine
Author(s) -
Adlercreutz Dietlind,
Wehtje Ernst
Publication year - 2004
Publication title -
journal of the american oil chemists' society
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.512
H-Index - 117
eISSN - 1558-9331
pISSN - 0003-021X
DOI - 10.1007/s11746-006-0940-5
Subject(s) - hexanoic acid , decanoic acid , yield (engineering) , chemistry , lipase , hydrolysis , phosphatidylcholine , enzyme , enzymatic hydrolysis , catalysis , palmitic acid , fatty acid , organic chemistry , chromatography , biochemistry , phospholipid , metallurgy , materials science , membrane
The enzymatic synthesis of PC with decanoic acid in the sn ‐1 and hexanoic acid in the sn ‐2 position is described. The procedure comprises the following enzymatic steps: (i) treatment of egg yolk with phospholipase A 2 (PLA 2 ) to hydrolyze egg yolk PC to 1‐acyl lysophosphatidylcholine (LPC); (ii) esterification of 1‐acyl LPC with hexanoic acid catalyzed by PLA 2 to yield PC with hexanoic acid in the sn ‐2 position; (iii) removal of the FA in the sn ‐1 position by lipase‐catalyzed ethanolysis to yield 2‐hexanoyl LPC; and finally (iv) introduction of decanoic acid in this position by lipase‐catalyzed esterification of 2‐hexanoyl LPC to yield 1‐decanoyl‐2‐hexanoyl‐PC. Two egg yolks with a weight of 16 g were required to obtain 160 mg of the desired product. The chemical purity of the PC product and the positional purity of the FA were around 99%. The method is applicable for the synthesis of other mixed‐acid PC species as well.