Lysophosphatidylcholine synthesis with Candida antarctica lipase B (Novozym 435)
(2000) In Enzyme and Microbial Technology 26(8). p.630-635- Abstract
Immobilized lipase from Candida antarctica lipase B (Novozym 435) was effective in the synthesis of lysophosphatidylcholine (LPC). The transesterification of L-α-glycerophosphorylcholine (GPC) and vinyl laurate was carried out in a solvent free system or in the presence of 50% (v/v) t- butanol. High conversions (>95%) were easily achieved. The lipase was selective for the sn-1 position of the glycerol backbone, and almost no phosphatidylcholine was produced in the first 24 hours of the reaction. However, and probably due to acyl migration, the formation of phosphatidylcholine (PC) increased slowly if the reactions were incubated over a long period of time. The synthetic reaction was only possible with a high excess of vinyl laurate... (More)
Immobilized lipase from Candida antarctica lipase B (Novozym 435) was effective in the synthesis of lysophosphatidylcholine (LPC). The transesterification of L-α-glycerophosphorylcholine (GPC) and vinyl laurate was carried out in a solvent free system or in the presence of 50% (v/v) t- butanol. High conversions (>95%) were easily achieved. The lipase was selective for the sn-1 position of the glycerol backbone, and almost no phosphatidylcholine was produced in the first 24 hours of the reaction. However, and probably due to acyl migration, the formation of phosphatidylcholine (PC) increased slowly if the reactions were incubated over a long period of time. The synthetic reaction was only possible with a high excess of vinyl laurate over glycerophosphorylcholine (>10 times). High purity products could be produced by a decrease of the reaction temperature to induce precipitation of the product. The temperature needed depended on the fatty acid chain length. Thus, only lysophosphatidylcholine was produced with palmitic acid vinyl ester at 45°C, whereas for the vinyl esters of lauric acid, capric acid, and caprylic acid, a lower reaction temperature (25°C) was necessary to obtain solely the lysophospholipid products. (C) 2000 Elsevier Science Inc.
(Less)
- author
- Virto, Carmen LU and Adlercreutz, Patrick LU
- organization
- publishing date
- 2000-05-01
- type
- Contribution to journal
- publication status
- published
- subject
- keywords
- Fatty acid vinyl ester, Lipase, Lysophosphatidylcholine, Phosphatidylcholine, Transesterification
- in
- Enzyme and Microbial Technology
- volume
- 26
- issue
- 8
- pages
- 6 pages
- publisher
- Elsevier
- external identifiers
-
- scopus:0033995879
- ISSN
- 0141-0229
- DOI
- 10.1016/S0141-0229(00)00147-2
- language
- English
- LU publication?
- yes
- id
- 2461b193-ad8e-4ae6-8eaa-68a9252d72cc
- date added to LUP
- 2019-06-20 15:56:48
- date last changed
- 2022-03-25 20:47:55
@article{2461b193-ad8e-4ae6-8eaa-68a9252d72cc, abstract = {{<p>Immobilized lipase from Candida antarctica lipase B (Novozym 435) was effective in the synthesis of lysophosphatidylcholine (LPC). The transesterification of L-α-glycerophosphorylcholine (GPC) and vinyl laurate was carried out in a solvent free system or in the presence of 50% (v/v) t- butanol. High conversions (>95%) were easily achieved. The lipase was selective for the sn-1 position of the glycerol backbone, and almost no phosphatidylcholine was produced in the first 24 hours of the reaction. However, and probably due to acyl migration, the formation of phosphatidylcholine (PC) increased slowly if the reactions were incubated over a long period of time. The synthetic reaction was only possible with a high excess of vinyl laurate over glycerophosphorylcholine (>10 times). High purity products could be produced by a decrease of the reaction temperature to induce precipitation of the product. The temperature needed depended on the fatty acid chain length. Thus, only lysophosphatidylcholine was produced with palmitic acid vinyl ester at 45°C, whereas for the vinyl esters of lauric acid, capric acid, and caprylic acid, a lower reaction temperature (25°C) was necessary to obtain solely the lysophospholipid products. (C) 2000 Elsevier Science Inc.</p>}}, author = {{Virto, Carmen and Adlercreutz, Patrick}}, issn = {{0141-0229}}, keywords = {{Fatty acid vinyl ester; Lipase; Lysophosphatidylcholine; Phosphatidylcholine; Transesterification}}, language = {{eng}}, month = {{05}}, number = {{8}}, pages = {{630--635}}, publisher = {{Elsevier}}, series = {{Enzyme and Microbial Technology}}, title = {{Lysophosphatidylcholine synthesis with Candida antarctica lipase B (Novozym 435)}}, url = {{http://dx.doi.org/10.1016/S0141-0229(00)00147-2}}, doi = {{10.1016/S0141-0229(00)00147-2}}, volume = {{26}}, year = {{2000}}, }