Lipase-catalyzed fatty acid exchange in digalactosyldiacylglycerol. Improvement of yield due to the addition of phenylboronic acid
(2000) In Biocatalysis and Biotransformation 18(1). p.1-12- Abstract
Rhizopus arrhizus lipase immobilized on porous polypropylene was used in an acidolysis reaction in toluene at low water activity (0.11) to exchange the fatty acid in the sn-1-position of digalactosyldiacylglycerol (DGDG). Without extra precautions, an yield of only about 20% was obtained, mainly due to side reactions; incorporation of an extra acyl group on the primary hydroxyl of the digalactosyl moiety and acyl migration in partially deacylated reaction intermediates, followed by further hydrolysis. By the addition of phenylboronic acid (equimolar amount with respect to DGDG) both the side reactions were suppressed and the yield of DGDG containing the new fatty acid (heptadecanoic acid) in the sn-1-position increased to about 60%.
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https://lup.lub.lu.se/record/e138455c-8648-4a49-8979-b00037a67173
- author
- Vaz, Silvia ; Persson, Mattias ; Svensson, Ingemar LU and Adlercreutz, Patrick LU
- organization
- publishing date
- 2000-01-01
- type
- Contribution to journal
- publication status
- published
- subject
- keywords
- Digalactosyldiacylglycerol, Galactolipid, Lipase, Phenylboronic acid
- in
- Biocatalysis and Biotransformation
- volume
- 18
- issue
- 1
- pages
- 12 pages
- publisher
- Taylor & Francis
- external identifiers
-
- scopus:0034003695
- ISSN
- 1024-2422
- DOI
- 10.3109/10242420009040119
- language
- English
- LU publication?
- yes
- id
- e138455c-8648-4a49-8979-b00037a67173
- date added to LUP
- 2019-06-20 15:55:52
- date last changed
- 2022-01-31 22:13:24
@article{e138455c-8648-4a49-8979-b00037a67173, abstract = {{<p>Rhizopus arrhizus lipase immobilized on porous polypropylene was used in an acidolysis reaction in toluene at low water activity (0.11) to exchange the fatty acid in the sn-1-position of digalactosyldiacylglycerol (DGDG). Without extra precautions, an yield of only about 20% was obtained, mainly due to side reactions; incorporation of an extra acyl group on the primary hydroxyl of the digalactosyl moiety and acyl migration in partially deacylated reaction intermediates, followed by further hydrolysis. By the addition of phenylboronic acid (equimolar amount with respect to DGDG) both the side reactions were suppressed and the yield of DGDG containing the new fatty acid (heptadecanoic acid) in the sn-1-position increased to about 60%.</p>}}, author = {{Vaz, Silvia and Persson, Mattias and Svensson, Ingemar and Adlercreutz, Patrick}}, issn = {{1024-2422}}, keywords = {{Digalactosyldiacylglycerol; Galactolipid; Lipase; Phenylboronic acid}}, language = {{eng}}, month = {{01}}, number = {{1}}, pages = {{1--12}}, publisher = {{Taylor & Francis}}, series = {{Biocatalysis and Biotransformation}}, title = {{Lipase-catalyzed fatty acid exchange in digalactosyldiacylglycerol. Improvement of yield due to the addition of phenylboronic acid}}, url = {{http://dx.doi.org/10.3109/10242420009040119}}, doi = {{10.3109/10242420009040119}}, volume = {{18}}, year = {{2000}}, }