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The enantiomeric purity of alcohols formed by enzymatic reduction of ketones can be improved by optimisation of the temperature and by using a high co-substrate concentration

Yang, Hong ; Jönsson, Åsa LU ; Wehtje, Ernst LU ; Adlercreutz, Patrick LU orcid and Mattiasson, Bo LU (1997) In Biochimica et Biophysica Acta - General Subjects 1336(1). p.51-58
Abstract

The stereoselective reduction of ketones by alcohol dehydrogenase from Thermoanaerobium brockii was studied in organic reaction media, 2-Propanol was used as co-substrate to regenerate the coenzyme NADPH. The enantiomeric excess of the alcohol formed from the ketone decreased during the course of the reaction (from 53 to 0% e.e. in the formation of (R)-2-butanol). This was interpreted as being due to the reversibility of all the reactions involved. By using a large excess of 2-propanol this effect was suppressed. In the reduction of 2-butanone to (R)-2-butanol, the enantiomeric excess increased with increasing temperature, but in the reduction of a-pentanone to (S)-2-pentanol the enantiomeric excess decreased with increasing... (More)

The stereoselective reduction of ketones by alcohol dehydrogenase from Thermoanaerobium brockii was studied in organic reaction media, 2-Propanol was used as co-substrate to regenerate the coenzyme NADPH. The enantiomeric excess of the alcohol formed from the ketone decreased during the course of the reaction (from 53 to 0% e.e. in the formation of (R)-2-butanol). This was interpreted as being due to the reversibility of all the reactions involved. By using a large excess of 2-propanol this effect was suppressed. In the reduction of 2-butanone to (R)-2-butanol, the enantiomeric excess increased with increasing temperature, but in the reduction of a-pentanone to (S)-2-pentanol the enantiomeric excess decreased with increasing temperature, The data were evaluated in terms of free energy of activation of the reaction pathways leading to the different possible products.

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author
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organization
publishing date
type
Contribution to journal
publication status
published
subject
in
Biochimica et Biophysica Acta - General Subjects
volume
1336
issue
1
pages
8 pages
publisher
Elsevier
external identifiers
  • pmid:9271250
  • scopus:0342601433
ISSN
0304-4165
DOI
10.1016/S0304-4165(97)00010-X
language
English
LU publication?
yes
id
130b140b-d20f-4973-974a-d350075487a7
date added to LUP
2019-06-20 16:13:53
date last changed
2024-01-16 03:20:25
@article{130b140b-d20f-4973-974a-d350075487a7,
  abstract     = {{<p>The stereoselective reduction of ketones by alcohol dehydrogenase from Thermoanaerobium brockii was studied in organic reaction media, 2-Propanol was used as co-substrate to regenerate the coenzyme NADPH. The enantiomeric excess of the alcohol formed from the ketone decreased during the course of the reaction (from 53 to 0% e.e. in the formation of (R)-2-butanol). This was interpreted as being due to the reversibility of all the reactions involved. By using a large excess of 2-propanol this effect was suppressed. In the reduction of 2-butanone to (R)-2-butanol, the enantiomeric excess increased with increasing temperature, but in the reduction of a-pentanone to (S)-2-pentanol the enantiomeric excess decreased with increasing temperature, The data were evaluated in terms of free energy of activation of the reaction pathways leading to the different possible products.</p>}},
  author       = {{Yang, Hong and Jönsson, Åsa and Wehtje, Ernst and Adlercreutz, Patrick and Mattiasson, Bo}},
  issn         = {{0304-4165}},
  language     = {{eng}},
  month        = {{07}},
  number       = {{1}},
  pages        = {{51--58}},
  publisher    = {{Elsevier}},
  series       = {{Biochimica et Biophysica Acta - General Subjects}},
  title        = {{The enantiomeric purity of alcohols formed by enzymatic reduction of ketones can be improved by optimisation of the temperature and by using a high co-substrate concentration}},
  url          = {{http://dx.doi.org/10.1016/S0304-4165(97)00010-X}},
  doi          = {{10.1016/S0304-4165(97)00010-X}},
  volume       = {{1336}},
  year         = {{1997}},
}