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Enzymatic and chemical synthesis of phosphatidylcholine regioisomers containing eicosapentaenoic acid or docosahexaenoic acid

Lyberg, Ann-Marie LU ; Adlercreutz, Dietlind LU and Adlercreutz, Patrick LU (2005) In European Journal of Lipid Science and Technology 107(5). p.279-290
Abstract
Regioselective incorporation of eicosapentaenoic acid (EPA) and docosahexaenoic acid (DHA) into phosphatidylcholine (PC) was carried out using enzymatic and chemical synthesis. Incorporation at the sn-1 position was successfully achieved by lipase-catalysed esterification of 2-palmitoyl-lysophosphatidylcholine (LPC), although in most cases, the enzymes incorporated EPA and DHA at lower rates than other fatty acids. For the incorporation of DHA, Candida antarctica lipase B was the only useful enzyme, while incorporation of EPA was efficiently carried out using either this enzyme or Rhizopus arrhizus lipase. The highest yields in the lipase-catalysed reactions were obtained at the lowest water activity (close to 0). However, by carrying out... (More)
Regioselective incorporation of eicosapentaenoic acid (EPA) and docosahexaenoic acid (DHA) into phosphatidylcholine (PC) was carried out using enzymatic and chemical synthesis. Incorporation at the sn-1 position was successfully achieved by lipase-catalysed esterification of 2-palmitoyl-lysophosphatidylcholine (LPC), although in most cases, the enzymes incorporated EPA and DHA at lower rates than other fatty acids. For the incorporation of DHA, Candida antarctica lipase B was the only useful enzyme, while incorporation of EPA was efficiently carried out using either this enzyme or Rhizopus arrhizus lipase. The highest yields in the lipase-catalysed reactions were obtained at the lowest water activity (close to 0). However, by carrying out the reactions at a higher water activity of 0.22, more EPA and DHA were incorporated. Esterification of 2-palmitoyl-LPC with pure EPA at this water activity converted 66 mol-% of LPC to PC using Rhizopus arrhizus lipase as catalyst. When the fatty acid was DHA and the catalyst Candida antarctica lipase B, 45 mol-% of PC was obtained. For incorporation of EPA and DHA at the sn-2 position, phospholipase A(2) was used, but the reaction was very slow. Chemical coupling of 1 -palmitoyl-LPC and EPA or DHA was more efficient, resulting in complete conversion of LPC. (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
107
issue
5
pages
279 - 290
publisher
John Wiley & Sons
external identifiers
  • wos:000229916500002
  • scopus:20444464408
ISSN
1438-7697
DOI
10.1002/ejlt.200501138
language
English
LU publication?
yes
id
906ba88c-f46b-4d3a-9584-be2a8bb35810 (old id 155135)
date added to LUP
2007-07-02 13:32:46
date last changed
2017-07-23 03:55:23
@article{906ba88c-f46b-4d3a-9584-be2a8bb35810,
  abstract     = {Regioselective incorporation of eicosapentaenoic acid (EPA) and docosahexaenoic acid (DHA) into phosphatidylcholine (PC) was carried out using enzymatic and chemical synthesis. Incorporation at the sn-1 position was successfully achieved by lipase-catalysed esterification of 2-palmitoyl-lysophosphatidylcholine (LPC), although in most cases, the enzymes incorporated EPA and DHA at lower rates than other fatty acids. For the incorporation of DHA, Candida antarctica lipase B was the only useful enzyme, while incorporation of EPA was efficiently carried out using either this enzyme or Rhizopus arrhizus lipase. The highest yields in the lipase-catalysed reactions were obtained at the lowest water activity (close to 0). However, by carrying out the reactions at a higher water activity of 0.22, more EPA and DHA were incorporated. Esterification of 2-palmitoyl-LPC with pure EPA at this water activity converted 66 mol-% of LPC to PC using Rhizopus arrhizus lipase as catalyst. When the fatty acid was DHA and the catalyst Candida antarctica lipase B, 45 mol-% of PC was obtained. For incorporation of EPA and DHA at the sn-2 position, phospholipase A(2) was used, but the reaction was very slow. Chemical coupling of 1 -palmitoyl-LPC and EPA or DHA was more efficient, resulting in complete conversion of LPC.},
  author       = {Lyberg, Ann-Marie and Adlercreutz, Dietlind and Adlercreutz, Patrick},
  issn         = {1438-7697},
  language     = {eng},
  number       = {5},
  pages        = {279--290},
  publisher    = {John Wiley & Sons},
  series       = {European Journal of Lipid Science and Technology},
  title        = {Enzymatic and chemical synthesis of phosphatidylcholine regioisomers containing eicosapentaenoic acid or docosahexaenoic acid},
  url          = {http://dx.doi.org/10.1002/ejlt.200501138},
  volume       = {107},
  year         = {2005},
}