An efficient and regioselective biocatalytic synthesis of aromatic N‐oxides by using a soluble di‐iron monooxygenase PmlABCDEF produced in the Pseudomonas species
| Autor: | Renata Gasparavičiūtė, Daiva Tauraitė, Vytautas Petkevičius, Rolandas Meškys, Justas Vaitekūnas |
|---|---|
| Jazyk: | angličtina |
| Rok vydání: | 2021 |
| Předmět: |
Pyrazine
Iron Bioengineering Applied Microbiology and Biotechnology Biochemistry Mixed Function Oxygenases 03 medical and health sciences chemistry.chemical_compound Pseudomonas Pyridine Organic chemistry Research Articles 030304 developmental biology 0303 health sciences biology Pseudomonas putida 030306 microbiology Substrate (chemistry) Regioselectivity Oxides biology.organism_classification chemistry Biocatalysis Yield (chemistry) chemoselectivity nitrogen heterocycles oxidation regioselectivity soluble di-iron monooxygenase TP248.13-248.65 Research Article Biotechnology |
| Zdroj: | Microbial Biotechnology, Vol 14, Iss 4, Pp 1771-1783 (2021) Microbial biotechnology, Hoboken : Wiley, 2021, vol. 14, iss. 4, p. 1771-1783 Microbial Biotechnology |
| ISSN: | 1751-7915 |
| Popis: | 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. In this study, we describe a new whole‐cell biocatalysis system for aromatic N‐oxides synthesis based on production of soluble di‐iron monooxygenase PmlABCDEF. Various pyridine, pyrazine, and pyrimidine derivatives could be converted into appropriate N‐oxides on a preparative scale in the simple shake‐flask cultivation. This improved synthesis method was used to yield specific pyrazine and pyrimidine oxidation products that were difficult to obtain by employing a standard mCPBA‐based technique. |
| Databáze: | OpenAIRE |
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