Stereoselective Bioreduction to a Chiral Building Block on a Kilogram Scale
The highly stereoselective bioreduction of ethyl cyclohexanone-2-carboxylate (1) on a kilogram scale is described. Ethyl(1S,2S)-trans-2-hydroxycyclohexane carboxylate (2) was prepared in 56% yield with a diastereomeric ratio (dr) of 99:1 and an enantiomeric ratio (er) of 99.5:0.5 after rec...
| Main Authors: | , , |
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| Format: | Article |
| Language: | deu |
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Swiss Chemical Society
2003-09-01
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| Series: | CHIMIA |
| Subjects: | |
| Online Access: | https://chimia.ch/chimia/article/view/3743 |
| _version_ | 1828181102357905408 |
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| author | Christelle Jablonski-Lorin Vito Melillo Ernst Hungerbühler |
| author_facet | Christelle Jablonski-Lorin Vito Melillo Ernst Hungerbühler |
| author_sort | Christelle Jablonski-Lorin |
| collection | DOAJ |
| description |
The highly stereoselective bioreduction of ethyl cyclohexanone-2-carboxylate (1) on a kilogram scale is described. Ethyl(1S,2S)-trans-2-hydroxycyclohexane carboxylate (2) was prepared in 56% yield with a diastereomeric ratio (dr) of 99:1 and an enantiomeric
ratio (er) of 99.5:0.5 after rectification. The cell growth and the biotransformation were performed in a large wave bioreactor equipped with a 200 l cell bag at Novartis Pharma AG, while the different purification steps were performed at the FHBB (Muttenz). The fourth semester chemistry students
at the FHBB were actively involved in the preparation and optimization of the entire process.
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| first_indexed | 2024-04-12T05:56:44Z |
| format | Article |
| id | doaj.art-0f115d433fa74999b80cc6557cfdf053 |
| institution | Directory Open Access Journal |
| issn | 0009-4293 2673-2424 |
| language | deu |
| last_indexed | 2024-04-12T05:56:44Z |
| publishDate | 2003-09-01 |
| publisher | Swiss Chemical Society |
| record_format | Article |
| series | CHIMIA |
| spelling | doaj.art-0f115d433fa74999b80cc6557cfdf0532022-12-22T03:45:08ZdeuSwiss Chemical SocietyCHIMIA0009-42932673-24242003-09-0157910.2533/000942903777678894Stereoselective Bioreduction to a Chiral Building Block on a Kilogram ScaleChristelle Jablonski-LorinVito MelilloErnst Hungerbühler The highly stereoselective bioreduction of ethyl cyclohexanone-2-carboxylate (1) on a kilogram scale is described. Ethyl(1S,2S)-trans-2-hydroxycyclohexane carboxylate (2) was prepared in 56% yield with a diastereomeric ratio (dr) of 99:1 and an enantiomeric ratio (er) of 99.5:0.5 after rectification. The cell growth and the biotransformation were performed in a large wave bioreactor equipped with a 200 l cell bag at Novartis Pharma AG, while the different purification steps were performed at the FHBB (Muttenz). The fourth semester chemistry students at the FHBB were actively involved in the preparation and optimization of the entire process. https://chimia.ch/chimia/article/view/3743BiotransformationHigh stereoselectivityScale-up processS. pombe yeastWavebioreactor |
| spellingShingle | Christelle Jablonski-Lorin Vito Melillo Ernst Hungerbühler Stereoselective Bioreduction to a Chiral Building Block on a Kilogram Scale CHIMIA Biotransformation High stereoselectivity Scale-up process S. pombe yeast Wavebioreactor |
| title | Stereoselective Bioreduction to a Chiral Building Block on a Kilogram Scale |
| title_full | Stereoselective Bioreduction to a Chiral Building Block on a Kilogram Scale |
| title_fullStr | Stereoselective Bioreduction to a Chiral Building Block on a Kilogram Scale |
| title_full_unstemmed | Stereoselective Bioreduction to a Chiral Building Block on a Kilogram Scale |
| title_short | Stereoselective Bioreduction to a Chiral Building Block on a Kilogram Scale |
| title_sort | stereoselective bioreduction to a chiral building block on a kilogram scale |
| topic | Biotransformation High stereoselectivity Scale-up process S. pombe yeast Wavebioreactor |
| url | https://chimia.ch/chimia/article/view/3743 |
| work_keys_str_mv | AT christellejablonskilorin stereoselectivebioreductiontoachiralbuildingblockonakilogramscale AT vitomelillo stereoselectivebioreductiontoachiralbuildingblockonakilogramscale AT ernsthungerbuhler stereoselectivebioreductiontoachiralbuildingblockonakilogramscale |