Candida antarctica lipase B-catalysed synthesis of dihydroxyacetone fatty acid esters
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 o...
Published in: | Biocatalysis and Biotransformation |
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Taylor & Francis
2000
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Online Access: | https://lup.lub.lu.se/record/550055c0-b34e-4b7b-9498-9ef7d7ffbced https://doi.org/10.3109/10242420009040120 |
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ftulundlup:oai:lup.lub.lu.se:550055c0-b34e-4b7b-9498-9ef7d7ffbced 2023-05-15T13:56:12+02:00 Candida antarctica lipase B-catalysed synthesis of dihydroxyacetone fatty acid esters Virto, Carmen Svensson, Ingemar Adlercreutz, Patrick 2000-01-01 https://lup.lub.lu.se/record/550055c0-b34e-4b7b-9498-9ef7d7ffbced https://doi.org/10.3109/10242420009040120 eng eng Taylor & Francis https://lup.lub.lu.se/record/550055c0-b34e-4b7b-9498-9ef7d7ffbced http://dx.doi.org/10.3109/10242420009040120 scopus:0033996072 Biocatalysis and Biotransformation; 18(1), pp 13-29 (2000) ISSN: 1024-2422 Biocatalysis and Enzyme Technology 1,3-Diacyl-dihydroxyacetone 1-Acyl-dihydroxyacetone Lipase Organic solvents contributiontojournal/article info:eu-repo/semantics/article text 2000 ftulundlup https://doi.org/10.3109/10242420009040120 2023-02-01T23:37:39Z 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. Article in Journal/Newspaper Antarc* Antarctica Lund University Publications (LUP) Biocatalysis and Biotransformation 18 1 13 29 |
institution |
Open Polar |
collection |
Lund University Publications (LUP) |
op_collection_id |
ftulundlup |
language |
English |
topic |
Biocatalysis and Enzyme Technology 1,3-Diacyl-dihydroxyacetone 1-Acyl-dihydroxyacetone Lipase Organic solvents |
spellingShingle |
Biocatalysis and Enzyme Technology 1,3-Diacyl-dihydroxyacetone 1-Acyl-dihydroxyacetone Lipase Organic solvents Virto, Carmen Svensson, Ingemar Adlercreutz, Patrick Candida antarctica lipase B-catalysed synthesis of dihydroxyacetone fatty acid esters |
topic_facet |
Biocatalysis and Enzyme Technology 1,3-Diacyl-dihydroxyacetone 1-Acyl-dihydroxyacetone Lipase Organic solvents |
description |
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. |
format |
Article in Journal/Newspaper |
author |
Virto, Carmen Svensson, Ingemar Adlercreutz, Patrick |
author_facet |
Virto, Carmen Svensson, Ingemar Adlercreutz, Patrick |
author_sort |
Virto, Carmen |
title |
Candida antarctica lipase B-catalysed synthesis of dihydroxyacetone fatty acid esters |
title_short |
Candida antarctica lipase B-catalysed synthesis of dihydroxyacetone fatty acid esters |
title_full |
Candida antarctica lipase B-catalysed synthesis of dihydroxyacetone fatty acid esters |
title_fullStr |
Candida antarctica lipase B-catalysed synthesis of dihydroxyacetone fatty acid esters |
title_full_unstemmed |
Candida antarctica lipase B-catalysed synthesis of dihydroxyacetone fatty acid esters |
title_sort |
candida antarctica lipase b-catalysed synthesis of dihydroxyacetone fatty acid esters |
publisher |
Taylor & Francis |
publishDate |
2000 |
url |
https://lup.lub.lu.se/record/550055c0-b34e-4b7b-9498-9ef7d7ffbced https://doi.org/10.3109/10242420009040120 |
genre |
Antarc* Antarctica |
genre_facet |
Antarc* Antarctica |
op_source |
Biocatalysis and Biotransformation; 18(1), pp 13-29 (2000) ISSN: 1024-2422 |
op_relation |
https://lup.lub.lu.se/record/550055c0-b34e-4b7b-9498-9ef7d7ffbced http://dx.doi.org/10.3109/10242420009040120 scopus:0033996072 |
op_doi |
https://doi.org/10.3109/10242420009040120 |
container_title |
Biocatalysis and Biotransformation |
container_volume |
18 |
container_issue |
1 |
container_start_page |
13 |
op_container_end_page |
29 |
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1766263570116378624 |