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Modification of the microenvironment of enzymes in organic solvents. Substitution of water by polar solvents

Reslow, Mats ; Adlercreutz, Patrick LU and Mattiasson, Bo LU (1992) In Biocatalysis and Biotransformation 6(4). p.307-318
Abstract

Enzyme catalysis in water-immiscible organic solvents is strongly influenced by the amount of water present in the reaction mixture. Effects of substitution of part of the water by other polar solvents were studied. In an alcoholysis reaction catalyzed by chymotrypsin deposited on celite, it was possible to exchange half of the water by formamide, ethylene glycol or dimethyl sulfoxide with often increased initial reaction rate. Furthermore, these substitutions caused the suppression of the competing hydrolysis reaction. However, formamide caused enzyme inactivation, and ethylene glycol participated as a reactant in the alcoholysis to some extent, hence dimethyl sulfoxide was considered the best water substitute among the solvents... (More)

Enzyme catalysis in water-immiscible organic solvents is strongly influenced by the amount of water present in the reaction mixture. Effects of substitution of part of the water by other polar solvents were studied. In an alcoholysis reaction catalyzed by chymotrypsin deposited on celite, it was possible to exchange half of the water by formamide, ethylene glycol or dimethyl sulfoxide with often increased initial reaction rate. Furthermore, these substitutions caused the suppression of the competing hydrolysis reaction. However, formamide caused enzyme inactivation, and ethylene glycol participated as a reactant in the alcoholysis to some extent, hence dimethyl sulfoxide was considered the best water substitute among the solvents tested. These effects were noted for chymotrypsin catalyzed alcoholysis in several water immiscible solvents and also for interesterification reactions catalyzed by Candida cylindracea lipase on celite. In the latter case a change in the stereoselectivity was observed. At a low water content a high stereoselectivity was observed; when the amount of polar solvent was increased, either by doubling the water content or adding an equal amount of DMSO, the stereoselectivity decreased.

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type
Contribution to journal
publication status
published
subject
keywords
Bioorganic synthesis, Enzymatic synthesis in organic media, Lipase, ╬▒chymotrypsin
in
Biocatalysis and Biotransformation
volume
6
issue
4
pages
12 pages
publisher
Taylor & Francis
external identifiers
  • scopus:0001585180
ISSN
1024-2422
DOI
10.3109/10242429209065250
language
English
LU publication?
yes
id
fef2010e-cfcb-497f-844c-b1f79aff8b28
date added to LUP
2019-06-22 18:41:21
date last changed
2020-01-13 02:05:07
@article{fef2010e-cfcb-497f-844c-b1f79aff8b28,
  abstract     = {<p>Enzyme catalysis in water-immiscible organic solvents is strongly influenced by the amount of water present in the reaction mixture. Effects of substitution of part of the water by other polar solvents were studied. In an alcoholysis reaction catalyzed by chymotrypsin deposited on celite, it was possible to exchange half of the water by formamide, ethylene glycol or dimethyl sulfoxide with often increased initial reaction rate. Furthermore, these substitutions caused the suppression of the competing hydrolysis reaction. However, formamide caused enzyme inactivation, and ethylene glycol participated as a reactant in the alcoholysis to some extent, hence dimethyl sulfoxide was considered the best water substitute among the solvents tested. These effects were noted for chymotrypsin catalyzed alcoholysis in several water immiscible solvents and also for interesterification reactions catalyzed by Candida cylindracea lipase on celite. In the latter case a change in the stereoselectivity was observed. At a low water content a high stereoselectivity was observed; when the amount of polar solvent was increased, either by doubling the water content or adding an equal amount of DMSO, the stereoselectivity decreased.</p>},
  author       = {Reslow, Mats and Adlercreutz, Patrick and Mattiasson, Bo},
  issn         = {1024-2422},
  language     = {eng},
  month        = {01},
  number       = {4},
  pages        = {307--318},
  publisher    = {Taylor & Francis},
  series       = {Biocatalysis and Biotransformation},
  title        = {Modification of the microenvironment of enzymes in organic solvents. Substitution of water by polar solvents},
  url          = {http://dx.doi.org/10.3109/10242429209065250},
  doi          = {10.3109/10242429209065250},
  volume       = {6},
  year         = {1992},
}