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)
Please use this url to cite or link to this publication:
https://lup.lub.lu.se/record/155135
- author
- Lyberg, Ann-Marie
LU
; Adlercreutz, Dietlind
LU
and Adlercreutz, Patrick
LU
- organization
- publishing date
- 2005
- 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 Inc.
- 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
- 2016-04-01 12:30:51
- date last changed
- 2022-04-13 19:55:21
@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 Inc.}},
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}},
doi = {{10.1002/ejlt.200501138}},
volume = {{107}},
year = {{2005}},
}