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An enzymatic method for the synthesis of mixed-acid phosphatidylcholine

Adlercreutz, Dietlind LU and Wehtje, Ernst LU (2004) In Journal of the American Oil Chemists Society 81(6). p.553-557
Abstract
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 lysophosphaticlylcholine (LPC) (ii) esterification of I-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... (More)
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 lysophosphaticlylcholine (LPC) (ii) esterification of I-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. (Less)
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author
organization
publishing date
type
Contribution to journal
publication status
published
subject
in
Journal of the American Oil Chemists Society
volume
81
issue
6
pages
553 - 557
publisher
The American Oil Chemists' Society
external identifiers
  • wos:000222709700006
  • scopus:3242747515
ISSN
0003-021X
DOI
10.1007/s11746-006-0940-5
language
English
LU publication?
yes
id
321d2aae-6a42-433e-931c-5c87f9e2c75d (old id 140632)
alternative location
http://www.aocs.org/press/jabs.asp?abs_id=3324&mo=6&yr=2004
date added to LUP
2007-06-26 09:09:12
date last changed
2017-10-01 03:59:18
@article{321d2aae-6a42-433e-931c-5c87f9e2c75d,
  abstract     = {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 lysophosphaticlylcholine (LPC) (ii) esterification of I-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.},
  author       = {Adlercreutz, Dietlind and Wehtje, Ernst},
  issn         = {0003-021X},
  language     = {eng},
  number       = {6},
  pages        = {553--557},
  publisher    = {The American Oil Chemists' Society},
  series       = {Journal of the American Oil Chemists Society},
  title        = {An enzymatic method for the synthesis of mixed-acid phosphatidylcholine},
  url          = {http://dx.doi.org/10.1007/s11746-006-0940-5},
  volume       = {81},
  year         = {2004},
}