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Lipase-catalyzed fatty acid exchange in digalactosyldiacylglycerol. Improvement of yield due to the addition of phenylboronic acid

Vaz, Silvia ; Persson, Mattias ; Svensson, Ingemar LU and Adlercreutz, Patrick LU (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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author
; ; and
organization
publishing date
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
2020-01-13 02:04:08
@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},
  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},
}