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Lysophosphatidylcholine synthesis with Candida antarctica lipase B (Novozym 435)

Virto, Carmen LU and Adlercreutz, Patrick LU (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.

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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
2020-09-30 06:15:31
@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 (&gt;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 (&gt;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},
  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},
}