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Candida antarctica lipase B-catalysed synthesis of dihydroxyacetone fatty acid esters

Virto, Carmen LU ; Svensson, Ingemar LU and Adlercreutz, Patrick LU (2000) In Biocatalysis and Biotransformation 18(1). p.13-29
Abstract

The enzymatic syntheses of 1-lauroyl-dihydroxyacetone and 1,3-dilauroyl-dihydroxyacetone were investigated. Lipase B from Candida antarctica (SP435) was used to catalyse the acylation of dihydroxyacetone (DHA) with lauric acid in organic solvent media at controlled water activity. High conversions of dihydroxyacetone (> 90%) are achieved when the water activity is 0.11 or below in solvents of various hydrophobicities, such as diethyl ether, methyl-tert-butyl ether (MTBE) and diphenyl ether. The main product in the esterification of DHA with lauric acid is 1-lauroyl-DHA, while the amount of 1,3-dilauroyl-DHA that is produced can be increased by changing the reaction conditions. Thus, decreasing the water activity from 0.75 to 0.06... (More)

The enzymatic syntheses of 1-lauroyl-dihydroxyacetone and 1,3-dilauroyl-dihydroxyacetone were investigated. Lipase B from Candida antarctica (SP435) was used to catalyse the acylation of dihydroxyacetone (DHA) with lauric acid in organic solvent media at controlled water activity. High conversions of dihydroxyacetone (> 90%) are achieved when the water activity is 0.11 or below in solvents of various hydrophobicities, such as diethyl ether, methyl-tert-butyl ether (MTBE) and diphenyl ether. The main product in the esterification of DHA with lauric acid is 1-lauroyl-DHA, while the amount of 1,3-dilauroyl-DHA that is produced can be increased by changing the reaction conditions. Thus, decreasing the water activity from 0.75 to 0.06 resulted in an increase in the total yield of 1,3-dilauroyl-DHA from 3% to 20%. Solvents which have high log P values favoured the acylation of 1-lauroyl-DHA and thereby the formation of 1,3-dilauroyl-DHA. Thus, when diphenyl ether was used in this reaction, the yield of 1,3-dilauroyl-DHA was 45%. Complete acylation to 1,3-dilauroyl-DHA was achieved when a fatty acid vinyl ester was used as acyl donor in a closed reactor.

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author
; and
organization
publishing date
type
Contribution to journal
publication status
published
subject
keywords
1,3-Diacyl-dihydroxyacetone, 1-Acyl-dihydroxyacetone, Lipase, Organic solvents
in
Biocatalysis and Biotransformation
volume
18
issue
1
pages
17 pages
publisher
Taylor & Francis
external identifiers
  • scopus:0033996072
ISSN
1024-2422
DOI
10.3109/10242420009040120
language
English
LU publication?
yes
id
550055c0-b34e-4b7b-9498-9ef7d7ffbced
date added to LUP
2019-06-20 15:56:21
date last changed
2020-01-13 02:04:15
@article{550055c0-b34e-4b7b-9498-9ef7d7ffbced,
  abstract     = {<p>The enzymatic syntheses of 1-lauroyl-dihydroxyacetone and 1,3-dilauroyl-dihydroxyacetone were investigated. Lipase B from Candida antarctica (SP435) was used to catalyse the acylation of dihydroxyacetone (DHA) with lauric acid in organic solvent media at controlled water activity. High conversions of dihydroxyacetone (&gt; 90%) are achieved when the water activity is 0.11 or below in solvents of various hydrophobicities, such as diethyl ether, methyl-tert-butyl ether (MTBE) and diphenyl ether. The main product in the esterification of DHA with lauric acid is 1-lauroyl-DHA, while the amount of 1,3-dilauroyl-DHA that is produced can be increased by changing the reaction conditions. Thus, decreasing the water activity from 0.75 to 0.06 resulted in an increase in the total yield of 1,3-dilauroyl-DHA from 3% to 20%. Solvents which have high log P values favoured the acylation of 1-lauroyl-DHA and thereby the formation of 1,3-dilauroyl-DHA. Thus, when diphenyl ether was used in this reaction, the yield of 1,3-dilauroyl-DHA was 45%. Complete acylation to 1,3-dilauroyl-DHA was achieved when a fatty acid vinyl ester was used as acyl donor in a closed reactor.</p>},
  author       = {Virto, Carmen and Svensson, Ingemar and Adlercreutz, Patrick},
  issn         = {1024-2422},
  language     = {eng},
  month        = {01},
  number       = {1},
  pages        = {13--29},
  publisher    = {Taylor & Francis},
  series       = {Biocatalysis and Biotransformation},
  title        = {Candida antarctica lipase B-catalysed synthesis of dihydroxyacetone fatty acid esters},
  url          = {http://dx.doi.org/10.3109/10242420009040120},
  doi          = {10.3109/10242420009040120},
  volume       = {18},
  year         = {2000},
}