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Microbial synthesis of a useful optically active (+)-isomer of lactone with bicyclo[4.3.0]nonane structure
Lactone 2a of a bicyclo[4.3.0]nonane structure is a good starting material for synthesis of many attractive compounds. Enantiomerically enriched (−)-(3aR,7aS)-lactone 2a is produced by whole cells of bacteria. In order to examine the impact of the absolute configuration on biological activity we eva...
Autores principales: | , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
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Nature Publishing Group UK
2018
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5765023/ https://www.ncbi.nlm.nih.gov/pubmed/29323184 http://dx.doi.org/10.1038/s41598-017-18876-9 |
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author | Boratyński, Filip Janik-Polanowicz, Agata Szczepańska, Ewa Olejniczak, Teresa |
author_facet | Boratyński, Filip Janik-Polanowicz, Agata Szczepańska, Ewa Olejniczak, Teresa |
author_sort | Boratyński, Filip |
collection | PubMed |
description | Lactone 2a of a bicyclo[4.3.0]nonane structure is a good starting material for synthesis of many attractive compounds. Enantiomerically enriched (−)-(3aR,7aS)-lactone 2a is produced by whole cells of bacteria. In order to examine the impact of the absolute configuration on biological activity we evaluated the process affording the opposite isomer. To this purpose Candida pelliculosa ZP22 characterized by high dehydrogenase activity was used. The goal of presented work was to perform bioreactor scale microbial one-pot oxidation of diol with selected yeast strain C. pelliculosa ZP22 to obtain chiral (+)-(3aS,7aR)-lactone 2a. The idea was to influence on alcohol dehydrogenase activity by increasing the activity of pro-(+)-ADH and simultanously diminishing the activity of pro-(−)-ADH. The optimization of biotransformation conditions involved the manipulation of the nutritional and physical parameters. Selection of the optimal medium in order to improve yield and process enantioselectivity was based on a two-level factorial design methodology. We have also studied the relationship between microbial growth and biosynthesis of lactone 2a. Preparative oxidation of diol 3a (400 mg/L, 2.9 mM) catalyzed by C. pelliculosa ZP22 in an optimized conditions afforded enantiomerically enriched (+)-(3aS,7aR)-isomer of lactone 2a with the isolated yield (30%). |
format | Online Article Text |
id | pubmed-5765023 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2018 |
publisher | Nature Publishing Group UK |
record_format | MEDLINE/PubMed |
spelling | pubmed-57650232018-01-17 Microbial synthesis of a useful optically active (+)-isomer of lactone with bicyclo[4.3.0]nonane structure Boratyński, Filip Janik-Polanowicz, Agata Szczepańska, Ewa Olejniczak, Teresa Sci Rep Article Lactone 2a of a bicyclo[4.3.0]nonane structure is a good starting material for synthesis of many attractive compounds. Enantiomerically enriched (−)-(3aR,7aS)-lactone 2a is produced by whole cells of bacteria. In order to examine the impact of the absolute configuration on biological activity we evaluated the process affording the opposite isomer. To this purpose Candida pelliculosa ZP22 characterized by high dehydrogenase activity was used. The goal of presented work was to perform bioreactor scale microbial one-pot oxidation of diol with selected yeast strain C. pelliculosa ZP22 to obtain chiral (+)-(3aS,7aR)-lactone 2a. The idea was to influence on alcohol dehydrogenase activity by increasing the activity of pro-(+)-ADH and simultanously diminishing the activity of pro-(−)-ADH. The optimization of biotransformation conditions involved the manipulation of the nutritional and physical parameters. Selection of the optimal medium in order to improve yield and process enantioselectivity was based on a two-level factorial design methodology. We have also studied the relationship between microbial growth and biosynthesis of lactone 2a. Preparative oxidation of diol 3a (400 mg/L, 2.9 mM) catalyzed by C. pelliculosa ZP22 in an optimized conditions afforded enantiomerically enriched (+)-(3aS,7aR)-isomer of lactone 2a with the isolated yield (30%). Nature Publishing Group UK 2018-01-11 /pmc/articles/PMC5765023/ /pubmed/29323184 http://dx.doi.org/10.1038/s41598-017-18876-9 Text en © The Author(s) 2017 Open Access This article is licensed under a Creative Commons Attribution 4.0 International License, which permits use, sharing, adaptation, distribution and reproduction in any medium or format, as long as you give appropriate credit to the original author(s) and the source, provide a link to the Creative Commons license, and indicate if changes were made. The images or other third party material in this article are included in the article’s Creative Commons license, unless indicated otherwise in a credit line to the material. If material is not included in the article’s Creative Commons license and your intended use is not permitted by statutory regulation or exceeds the permitted use, you will need to obtain permission directly from the copyright holder. To view a copy of this license, visit http://creativecommons.org/licenses/by/4.0/. |
spellingShingle | Article Boratyński, Filip Janik-Polanowicz, Agata Szczepańska, Ewa Olejniczak, Teresa Microbial synthesis of a useful optically active (+)-isomer of lactone with bicyclo[4.3.0]nonane structure |
title | Microbial synthesis of a useful optically active (+)-isomer of lactone with bicyclo[4.3.0]nonane structure |
title_full | Microbial synthesis of a useful optically active (+)-isomer of lactone with bicyclo[4.3.0]nonane structure |
title_fullStr | Microbial synthesis of a useful optically active (+)-isomer of lactone with bicyclo[4.3.0]nonane structure |
title_full_unstemmed | Microbial synthesis of a useful optically active (+)-isomer of lactone with bicyclo[4.3.0]nonane structure |
title_short | Microbial synthesis of a useful optically active (+)-isomer of lactone with bicyclo[4.3.0]nonane structure |
title_sort | microbial synthesis of a useful optically active (+)-isomer of lactone with bicyclo[4.3.0]nonane structure |
topic | Article |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5765023/ https://www.ncbi.nlm.nih.gov/pubmed/29323184 http://dx.doi.org/10.1038/s41598-017-18876-9 |
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