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Enzymatic synthesis of lysophosphatidic acid and phosphatidic acid

Virto, Carmen LU ; Svensson, Ingemar LU and Adlercreutz, Patrick LU orcid (1999) In Enzyme and Microbial Technology 24(10). p.651-658
Abstract

Immobilised 1,3-specific lipase from Rhizopus arrhizus was used as catalyst for the esterification of dl-glycero-3-phosphate and fatty acid or fatty acid vinyl ester in a solvent-free system. With lauric acid vinyl ester as acyl donor, a(w)<0.53 favored the synthesis of lysophosphatidic acid (1-acyl-rac-glycero-3-phosphate, LPA1) and the spontaneous acyl migration of the fatty acid on the molecule. Subsequent acylation by the enzyme resulted in high phosphatidic acid (1,2-diacyl-rac-glycero-3-phosphate, PA) formation and high total conversions (>95%). With oleic acid, maximum conversions of 55% were obtained at low water activities. Temperatures below melting point of the product favored precipitation and resulted in high final... (More)

Immobilised 1,3-specific lipase from Rhizopus arrhizus was used as catalyst for the esterification of dl-glycero-3-phosphate and fatty acid or fatty acid vinyl ester in a solvent-free system. With lauric acid vinyl ester as acyl donor, a(w)<0.53 favored the synthesis of lysophosphatidic acid (1-acyl-rac-glycero-3-phosphate, LPA1) and the spontaneous acyl migration of the fatty acid on the molecule. Subsequent acylation by the enzyme resulted in high phosphatidic acid (1,2-diacyl-rac-glycero-3-phosphate, PA) formation and high total conversions (>95%). With oleic acid, maximum conversions of 55% were obtained at low water activities. Temperatures below melting point of the product favored precipitation and resulted in high final conversion and high product ratio [LPA/(PA+LPA)]. Thus, LPA was the only product with lauric acid vinyl ester as acyl donor at 25°C. Increased substrate ratio (dl-glycero-3-phosphate/fatty acid) from 0.05 to 1 resulted in a higher ratio of LPA to PA formed, but a lower total conversion of dl-glycero-3-phosphate. Increased amounts of enzyme preparation did not result in higher esterification rates, probably due to high mass-transfer limitations. Copyright (C) 1999 Elsevier Science Inc. All rights reserved.

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author
; and
organization
publishing date
type
Contribution to journal
publication status
published
subject
keywords
DL-glycero-3-phosphate, Esterification, Fatty acid vinyl ester, Lipase, Lysophosphatidic acid, Phosphatidic acid
in
Enzyme and Microbial Technology
volume
24
issue
10
pages
8 pages
publisher
Elsevier
external identifiers
  • scopus:0032926698
ISSN
0141-0229
DOI
10.1016/S0141-0229(98)00153-7
language
English
LU publication?
yes
id
335e45c1-22ce-4997-8d82-44c598568d00
date added to LUP
2019-06-20 16:02:06
date last changed
2022-01-31 22:13:25
@article{335e45c1-22ce-4997-8d82-44c598568d00,
  abstract     = {{<p>Immobilised 1,3-specific lipase from Rhizopus arrhizus was used as catalyst for the esterification of dl-glycero-3-phosphate and fatty acid or fatty acid vinyl ester in a solvent-free system. With lauric acid vinyl ester as acyl donor, a(w)&lt;0.53 favored the synthesis of lysophosphatidic acid (1-acyl-rac-glycero-3-phosphate, LPA1) and the spontaneous acyl migration of the fatty acid on the molecule. Subsequent acylation by the enzyme resulted in high phosphatidic acid (1,2-diacyl-rac-glycero-3-phosphate, PA) formation and high total conversions (&gt;95%). With oleic acid, maximum conversions of 55% were obtained at low water activities. Temperatures below melting point of the product favored precipitation and resulted in high final conversion and high product ratio [LPA/(PA+LPA)]. Thus, LPA was the only product with lauric acid vinyl ester as acyl donor at 25°C. Increased substrate ratio (dl-glycero-3-phosphate/fatty acid) from 0.05 to 1 resulted in a higher ratio of LPA to PA formed, but a lower total conversion of dl-glycero-3-phosphate. Increased amounts of enzyme preparation did not result in higher esterification rates, probably due to high mass-transfer limitations. Copyright (C) 1999 Elsevier Science Inc. All rights reserved.</p>}},
  author       = {{Virto, Carmen and Svensson, Ingemar and Adlercreutz, Patrick}},
  issn         = {{0141-0229}},
  keywords     = {{DL-glycero-3-phosphate; Esterification; Fatty acid vinyl ester; Lipase; Lysophosphatidic acid; Phosphatidic acid}},
  language     = {{eng}},
  month        = {{07}},
  number       = {{10}},
  pages        = {{651--658}},
  publisher    = {{Elsevier}},
  series       = {{Enzyme and Microbial Technology}},
  title        = {{Enzymatic synthesis of lysophosphatidic acid and phosphatidic acid}},
  url          = {{http://dx.doi.org/10.1016/S0141-0229(98)00153-7}},
  doi          = {{10.1016/S0141-0229(98)00153-7}},
  volume       = {{24}},
  year         = {{1999}},
}