An efficient and regioselective biocatalytic synthesis of aromatic N‐oxides by using a soluble di‐iron monooxygenase PmlABCDEF produced in the Pseudomonas species
Summary Here, we present an improved whole‐cell biocatalysis system for the synthesis of heteroaromatic N‐oxides based on the production of a soluble di‐iron monooxygenase PmlABCDEF in Pseudomonas sp. MIL9 and Pseudomonas putida KT2440. The presented biocatalysis system performs under environmentall...
| Main Authors: | , , , , |
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| Format: | Article |
| Language: | English |
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Wiley
2021-07-01
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| Series: | Microbial Biotechnology |
| Online Access: | https://doi.org/10.1111/1751-7915.13849 |
| _version_ | 1819199236158259200 |
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| author | Vytautas Petkevičius Justas Vaitekūnas Renata Gasparavičiūtė Daiva Tauraitė Rolandas Meškys |
| author_facet | Vytautas Petkevičius Justas Vaitekūnas Renata Gasparavičiūtė Daiva Tauraitė Rolandas Meškys |
| author_sort | Vytautas Petkevičius |
| collection | DOAJ |
| description | Summary Here, we present an improved whole‐cell biocatalysis system for the synthesis of heteroaromatic N‐oxides based on the production of a soluble di‐iron monooxygenase PmlABCDEF in Pseudomonas sp. MIL9 and Pseudomonas putida KT2440. The presented biocatalysis system performs under environmentally benign conditions, features a straightforward and inexpensive procedure and possesses a high substrate conversion and product yield. The capacity of gram‐scale production was reached in the simple shake‐flask cultivation. The template substrates (pyridine, pyrazine, 2‐aminopyrimidine) have been converted into pyridine‐1‐oxide, pyrazine‐1‐oxide and 2‐aminopyrimidine‐1‐oxide in product titres of 18.0, 19.1 and 18.3 g l‐1, respectively. To our knowledge, this is the highest reported productivity of aromatic N‐oxides using biocatalysis methods. Moreover, comparing to the chemical method of aromatic N‐oxides synthesis based on meta‐chloroperoxybenzoic acid, the developed approach is applicable for a regioselective oxidation that is an additional advantageous option in the preparation of the anticipated N‐oxides. |
| first_indexed | 2024-12-23T03:13:07Z |
| format | Article |
| id | doaj.art-69c5c81e7c6a4935988ee2ac010b407c |
| institution | Directory Open Access Journal |
| issn | 1751-7915 |
| language | English |
| last_indexed | 2024-12-23T03:13:07Z |
| publishDate | 2021-07-01 |
| publisher | Wiley |
| record_format | Article |
| series | Microbial Biotechnology |
| spelling | doaj.art-69c5c81e7c6a4935988ee2ac010b407c2022-12-21T18:02:13ZengWileyMicrobial Biotechnology1751-79152021-07-011441771178310.1111/1751-7915.13849An efficient and regioselective biocatalytic synthesis of aromatic N‐oxides by using a soluble di‐iron monooxygenase PmlABCDEF produced in the Pseudomonas speciesVytautas Petkevičius0Justas Vaitekūnas1Renata Gasparavičiūtė2Daiva Tauraitė3Rolandas Meškys4Department of Molecular Microbiology and Biotechnology Institute of Biochemistry Life Sciences Center Vilnius University Saulėtekio 7 Vilnius LT‐10257 LithuaniaDepartment of Molecular Microbiology and Biotechnology Institute of Biochemistry Life Sciences Center Vilnius University Saulėtekio 7 Vilnius LT‐10257 LithuaniaDepartment of Molecular Microbiology and Biotechnology Institute of Biochemistry Life Sciences Center Vilnius University Saulėtekio 7 Vilnius LT‐10257 LithuaniaDepartment of Molecular Microbiology and Biotechnology Institute of Biochemistry Life Sciences Center Vilnius University Saulėtekio 7 Vilnius LT‐10257 LithuaniaDepartment of Molecular Microbiology and Biotechnology Institute of Biochemistry Life Sciences Center Vilnius University Saulėtekio 7 Vilnius LT‐10257 LithuaniaSummary Here, we present an improved whole‐cell biocatalysis system for the synthesis of heteroaromatic N‐oxides based on the production of a soluble di‐iron monooxygenase PmlABCDEF in Pseudomonas sp. MIL9 and Pseudomonas putida KT2440. The presented biocatalysis system performs under environmentally benign conditions, features a straightforward and inexpensive procedure and possesses a high substrate conversion and product yield. The capacity of gram‐scale production was reached in the simple shake‐flask cultivation. The template substrates (pyridine, pyrazine, 2‐aminopyrimidine) have been converted into pyridine‐1‐oxide, pyrazine‐1‐oxide and 2‐aminopyrimidine‐1‐oxide in product titres of 18.0, 19.1 and 18.3 g l‐1, respectively. To our knowledge, this is the highest reported productivity of aromatic N‐oxides using biocatalysis methods. Moreover, comparing to the chemical method of aromatic N‐oxides synthesis based on meta‐chloroperoxybenzoic acid, the developed approach is applicable for a regioselective oxidation that is an additional advantageous option in the preparation of the anticipated N‐oxides.https://doi.org/10.1111/1751-7915.13849 |
| spellingShingle | Vytautas Petkevičius Justas Vaitekūnas Renata Gasparavičiūtė Daiva Tauraitė Rolandas Meškys An efficient and regioselective biocatalytic synthesis of aromatic N‐oxides by using a soluble di‐iron monooxygenase PmlABCDEF produced in the Pseudomonas species Microbial Biotechnology |
| title | An efficient and regioselective biocatalytic synthesis of aromatic N‐oxides by using a soluble di‐iron monooxygenase PmlABCDEF produced in the Pseudomonas species |
| title_full | An efficient and regioselective biocatalytic synthesis of aromatic N‐oxides by using a soluble di‐iron monooxygenase PmlABCDEF produced in the Pseudomonas species |
| title_fullStr | An efficient and regioselective biocatalytic synthesis of aromatic N‐oxides by using a soluble di‐iron monooxygenase PmlABCDEF produced in the Pseudomonas species |
| title_full_unstemmed | An efficient and regioselective biocatalytic synthesis of aromatic N‐oxides by using a soluble di‐iron monooxygenase PmlABCDEF produced in the Pseudomonas species |
| title_short | An efficient and regioselective biocatalytic synthesis of aromatic N‐oxides by using a soluble di‐iron monooxygenase PmlABCDEF produced in the Pseudomonas species |
| title_sort | efficient and regioselective biocatalytic synthesis of aromatic n oxides by using a soluble di iron monooxygenase pmlabcdef produced in the pseudomonas species |
| url | https://doi.org/10.1111/1751-7915.13849 |
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