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Enzymatic fatty acid exchange in glycerophospholipids

Adlercreutz, Patrick LU ; Lyberg, Ann-Marie LU and Adlercreutz, Dietlind LU (2003) In European Journal of Lipid Science and Technology 105(10). p.638-645
Abstract
Lipases can be used to exchange fatty acids in the sn-1 position of glycerophospholipids and phospholipase A2 is useful for the corresponding exchange reaction in the sn-2 position. In both cases, the exchange can be done in a one-step acidolysis process or in a two-step process. In the latter case, the original fatty acid in the desired position is removed by enzymatic hydrolysis or alcoholysis and after isolation of the resulting lysophospholipid, the new fatty acid is introduced, using the same enzyme, in an esterification reaction. Several synthesis examples from the literature are reviewed. Incorporation of a new fatty acid into the sn-1 position is more favourable than incorporation into the sn-2 position because of the magnitudes of... (More)
Lipases can be used to exchange fatty acids in the sn-1 position of glycerophospholipids and phospholipase A2 is useful for the corresponding exchange reaction in the sn-2 position. In both cases, the exchange can be done in a one-step acidolysis process or in a two-step process. In the latter case, the original fatty acid in the desired position is removed by enzymatic hydrolysis or alcoholysis and after isolation of the resulting lysophospholipid, the new fatty acid is introduced, using the same enzyme, in an esterification reaction. Several synthesis examples from the literature are reviewed. Incorporation of a new fatty acid into the sn-1 position is more favourable than incorporation into the sn-2 position because of the magnitudes of the equilibrium constants of the reactions and because lipases can be used at much lower water activity than phospholipase A2. With the consecutive use of both enzymes highly pure products with defined fatty acids in both positions can be obtained. (Less)
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author
organization
publishing date
type
Contribution to journal
publication status
published
subject
in
European Journal of Lipid Science and Technology
volume
105
issue
10
pages
638 - 645
publisher
John Wiley & Sons
external identifiers
  • wos:000185995100013
  • scopus:0242266573
ISSN
1438-7697
DOI
10.1002/ejlt.200300832
language
English
LU publication?
yes
id
d556d85c-9942-41a1-b10a-ee97649286fe (old id 129028)
date added to LUP
2007-06-26 09:28:18
date last changed
2018-05-29 09:44:58
@article{d556d85c-9942-41a1-b10a-ee97649286fe,
  abstract     = {Lipases can be used to exchange fatty acids in the sn-1 position of glycerophospholipids and phospholipase A2 is useful for the corresponding exchange reaction in the sn-2 position. In both cases, the exchange can be done in a one-step acidolysis process or in a two-step process. In the latter case, the original fatty acid in the desired position is removed by enzymatic hydrolysis or alcoholysis and after isolation of the resulting lysophospholipid, the new fatty acid is introduced, using the same enzyme, in an esterification reaction. Several synthesis examples from the literature are reviewed. Incorporation of a new fatty acid into the sn-1 position is more favourable than incorporation into the sn-2 position because of the magnitudes of the equilibrium constants of the reactions and because lipases can be used at much lower water activity than phospholipase A2. With the consecutive use of both enzymes highly pure products with defined fatty acids in both positions can be obtained.},
  author       = {Adlercreutz, Patrick and Lyberg, Ann-Marie and Adlercreutz, Dietlind},
  issn         = {1438-7697},
  language     = {eng},
  number       = {10},
  pages        = {638--645},
  publisher    = {John Wiley & Sons},
  series       = {European Journal of Lipid Science and Technology},
  title        = {Enzymatic fatty acid exchange in glycerophospholipids},
  url          = {http://dx.doi.org/10.1002/ejlt.200300832},
  volume       = {105},
  year         = {2003},
}