Phosphonates enantiomers receiving with fungal enzymatic systems
Abstract Background Phosphonates derivatives are in the area of interests because of their unique chemical-physical features. These compounds manifest variety of biological interactions within the sensitive living cells, including impact on particular enzymes activities. Biological “cause and effect...
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| Format: | Article |
| Language: | English |
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BMC
2021-04-01
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| Series: | Microbial Cell Factories |
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| Online Access: | https://doi.org/10.1186/s12934-021-01573-8 |
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| author | Monika Serafin-Lewańczuk Małgorzata Brzezińska-Rodak Katarzyna Lubiak-Kozłowska Paulina Majewska Magdalena Klimek-Ochab Tomasz K. Olszewski Ewa Żymańczyk-Duda |
| author_facet | Monika Serafin-Lewańczuk Małgorzata Brzezińska-Rodak Katarzyna Lubiak-Kozłowska Paulina Majewska Magdalena Klimek-Ochab Tomasz K. Olszewski Ewa Żymańczyk-Duda |
| author_sort | Monika Serafin-Lewańczuk |
| collection | DOAJ |
| description | Abstract Background Phosphonates derivatives are in the area of interests because of their unique chemical-physical features. These compounds manifest variety of biological interactions within the sensitive living cells, including impact on particular enzymes activities. Biological “cause and effect” interactions are based upon the specific matching between the structures and/or compounds and this is usually the result of proper optical configurations of particular chiral moieties. Presented research is targeted to the phosphonates with the heteroatom incorporated in their side functionalities. Such molecules are described as possible substrates of bioconversion for the first time lately and this field is not fully explored. Results Presented research is targeted to the synthesis of pure hetero-phosphonates enantiomers. The catalytic activity of yeasts and moulds were tested towards two substrates: the thienyl and imidazole phosphonates to resolve their racemic mixtures. Biotransformations conditions differed depending on the outcome, what included changing of following parameters: type of cultivation media, bioprocess duration (24–72 h), additional biocatalyst pre-treatment (24–48 h starvation step triggering the secondary metabolism). (S)-1-amino-1-(3-thienyl)methylphosphonate was produced with the assistance of R. mucilaginosa or A. niger (e.e. up to 98% and yield up to 100%), starting from the 3 mM of substrate racemic mixture. Bioconversion of racemic mixture of 3 mM of (1-amino-1-(4-imidazole)methylphosphonic acid) resulted in the synthesis of S-isomer (up to 95% of e.e.; 100% of yield) with assistance of R. mucilaginosa. 24 h biotransformation was conducted with biomass preincubated under 48-hour starvation conditions. Such stereoselective resolution of the racemic mixtures of substrates undergoes under kinetic control with the conversion of one from the enantiomers. Conclusions Composition of the culturing media and pre-incubation in conditions of nutrient deficiency were significant factors influencing the results of kinetic resolution of racemic mixtures of phosphonic substrates and influencing the economic side of the biocatalysis e.g. by determining the duration of whole biocatalytic process. Graphical abstract |
| first_indexed | 2024-12-13T12:38:11Z |
| format | Article |
| id | doaj.art-4c753678f65e438893d9fa43a979b159 |
| institution | Directory Open Access Journal |
| issn | 1475-2859 |
| language | English |
| last_indexed | 2024-12-13T12:38:11Z |
| publishDate | 2021-04-01 |
| publisher | BMC |
| record_format | Article |
| series | Microbial Cell Factories |
| spelling | doaj.art-4c753678f65e438893d9fa43a979b1592022-12-21T23:45:44ZengBMCMicrobial Cell Factories1475-28592021-04-0120111410.1186/s12934-021-01573-8Phosphonates enantiomers receiving with fungal enzymatic systemsMonika Serafin-Lewańczuk0Małgorzata Brzezińska-Rodak1Katarzyna Lubiak-Kozłowska2Paulina Majewska3Magdalena Klimek-Ochab4Tomasz K. Olszewski5Ewa Żymańczyk-Duda6Department of Biochemistry, Molecular Biology and Biotechnology, Laboratory of Biotechnology, Wrocław University of Science and TechnologyDepartment of Biochemistry, Molecular Biology and Biotechnology, Laboratory of Biotechnology, Wrocław University of Science and TechnologyDepartment of Biochemistry, Molecular Biology and Biotechnology, Laboratory of Biotechnology, Wrocław University of Science and TechnologyDepartment of Biochemistry, Molecular Biology and Biotechnology, Laboratory of Biotechnology, Wrocław University of Science and TechnologyDepartment of Biochemistry, Molecular Biology and Biotechnology, Laboratory of Biotechnology, Wrocław University of Science and TechnologyDepartment of Physical and Quantum Chemistry, Wrocław University of Science and TechnologyDepartment of Biochemistry, Molecular Biology and Biotechnology, Laboratory of Biotechnology, Wrocław University of Science and TechnologyAbstract Background Phosphonates derivatives are in the area of interests because of their unique chemical-physical features. These compounds manifest variety of biological interactions within the sensitive living cells, including impact on particular enzymes activities. Biological “cause and effect” interactions are based upon the specific matching between the structures and/or compounds and this is usually the result of proper optical configurations of particular chiral moieties. Presented research is targeted to the phosphonates with the heteroatom incorporated in their side functionalities. Such molecules are described as possible substrates of bioconversion for the first time lately and this field is not fully explored. Results Presented research is targeted to the synthesis of pure hetero-phosphonates enantiomers. The catalytic activity of yeasts and moulds were tested towards two substrates: the thienyl and imidazole phosphonates to resolve their racemic mixtures. Biotransformations conditions differed depending on the outcome, what included changing of following parameters: type of cultivation media, bioprocess duration (24–72 h), additional biocatalyst pre-treatment (24–48 h starvation step triggering the secondary metabolism). (S)-1-amino-1-(3-thienyl)methylphosphonate was produced with the assistance of R. mucilaginosa or A. niger (e.e. up to 98% and yield up to 100%), starting from the 3 mM of substrate racemic mixture. Bioconversion of racemic mixture of 3 mM of (1-amino-1-(4-imidazole)methylphosphonic acid) resulted in the synthesis of S-isomer (up to 95% of e.e.; 100% of yield) with assistance of R. mucilaginosa. 24 h biotransformation was conducted with biomass preincubated under 48-hour starvation conditions. Such stereoselective resolution of the racemic mixtures of substrates undergoes under kinetic control with the conversion of one from the enantiomers. Conclusions Composition of the culturing media and pre-incubation in conditions of nutrient deficiency were significant factors influencing the results of kinetic resolution of racemic mixtures of phosphonic substrates and influencing the economic side of the biocatalysis e.g. by determining the duration of whole biocatalytic process. Graphical abstracthttps://doi.org/10.1186/s12934-021-01573-8BiotransformationHeterocyclic phosphonatesFungiYeast |
| spellingShingle | Monika Serafin-Lewańczuk Małgorzata Brzezińska-Rodak Katarzyna Lubiak-Kozłowska Paulina Majewska Magdalena Klimek-Ochab Tomasz K. Olszewski Ewa Żymańczyk-Duda Phosphonates enantiomers receiving with fungal enzymatic systems Microbial Cell Factories Biotransformation Heterocyclic phosphonates Fungi Yeast |
| title | Phosphonates enantiomers receiving with fungal enzymatic systems |
| title_full | Phosphonates enantiomers receiving with fungal enzymatic systems |
| title_fullStr | Phosphonates enantiomers receiving with fungal enzymatic systems |
| title_full_unstemmed | Phosphonates enantiomers receiving with fungal enzymatic systems |
| title_short | Phosphonates enantiomers receiving with fungal enzymatic systems |
| title_sort | phosphonates enantiomers receiving with fungal enzymatic systems |
| topic | Biotransformation Heterocyclic phosphonates Fungi Yeast |
| url | https://doi.org/10.1186/s12934-021-01573-8 |
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