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
(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.
(Less)
- author
- Yang, Hong ; Jönsson, Åsa LU ; Wehtje, Ernst LU ; Adlercreutz, Patrick LU and Mattiasson, Bo LU
- organization
- publishing date
- 1997-07-19
- 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}}, }