Microbial transformation of azaarenes and potential uses in pharmaceutical synthesis

Parshikov, Igor A.; Netrusov, A. I.; Sutherland, John B.

doi:10.1007/s00253-012-4220-z

Cited by 21 publications

(13 citation statements)

References 121 publications

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“…Many microorganisms possessing different N -heterocycle degradation pathways have previously been isolated2728. Meanwhile, microbial catabolism of N -heterocycles produces a lot of intermediates, which provide a huge pool of building blocks for the synthesis of agrochemicals and pharmaceuticals22930. In some cases, the synthesis and modification of these intermediates are difficult via organic chemistry methods.…”

Section: Discussionmentioning

confidence: 99%

“…DSM6336 has the capacity to transform 2-cyanopyrazine to 5-hydoxypyrazine-2-carboxylic acid41, which can be used for the synthesis of 5-chloropyrazine-2-carboxylic acid esters. (16–20) Microbial degradation of quinoline and isoquinoline produces several intermediates, and these intermediates also have potential uses in pharmaceutical synthesis30. Solid-lined arrows: biological processes.…”

Section: Figurementioning

confidence: 99%

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Green strategy from waste to value-added-chemical production: efficient biosynthesis of 6-hydroxy-3-succinoyl-pyridine by an engineered biocatalyst

Tang

2014

Sci Rep

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Value-added intermediates produced by microorganisms during the catabolism of N-heterocycles are potential building blocks for agrochemical synthesis and pharmaceutical production. 6-Hydroxy-3-succinoyl-pyridine (HSP), an intermediate in nicotine degradation, is an important precursor for the synthesis of drugs and compounds with biological activities. In the present study, we show that an engineered biocatalyst, Pseudomonas putida P-HSP, efficiently produced HSP from the renewable raw material of tobacco-waste that contains a high concentration of nicotine. The genetically constructed strain P-HSP realized a high accumulation of HSP, and HSP production was 3.7-fold higher than the non-engineered strain S16. Under optimal conditions, HSP was produced at high concentrations of 6.8 g l−1 and 16.3 g l−1 from tobacco-waste and nicotine, respectively. This work demonstrates a green strategy to block the catabolic pathway of N-heterocycles, which is a promising approach for the mutasynthesis of valuable compounds.

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Section: Discussionmentioning

confidence: 99%

Section: Figurementioning

confidence: 99%

Green strategy from waste to value-added-chemical production: efficient biosynthesis of 6-hydroxy-3-succinoyl-pyridine by an engineered biocatalyst

Tang

2014

Sci Rep

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“…Many nitrogen-containing aromatic compounds have been shown to be metabolized by fungi (Parshikov et al 2012). Strains of A. niger have been used for some of these biotransformations.…”

Section: Transformation Of Azaarenesmentioning

confidence: 99%

Biotransformations of organic compounds mediated by cultures of Aspergillus niger

Parshikov

Woodling

Sutherland

2015

Appl Microbiol Biotechnol

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Many different organic compounds may be converted by microbial biotransformation to high-value products for the chemical and pharmaceutical industries. This review summarizes the use of strains of Aspergillus niger, a well-known filamentous fungus used in numerous biotechnological processes, for biochemical transformations of organic compounds. The substrates transformed include monocyclic, bicyclic, and polycyclic aromatic hydrocarbons; azaarenes, epoxides, chlorinated hydrocarbons, and other aliphatic and aromatic compounds. The types of reactions performed by A. niger, although not unique to this species, are extremely diverse. They include hydroxylation, oxidation of various functional groups, reduction of double bonds, demethylation, sulfation, epoxide hydrolysis, dechlorination, ring cleavage, and conjugation. Some of the products may be useful as new investigational drugs or chemical intermediates.

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“…The formation of pyridine N -oxides has been observed in fungi Cunninghamella elegans ATCC 2626941, Verticillium sp. GF3931, and other fungi42 as well as in bacteria Methylococcus capsulatus 29 and Diaphorobacter sp. J5-5143.…”

Section: Resultsmentioning

confidence: 99%

Oxyfunctionalization of pyridine derivatives using whole cells of Burkholderia sp. MAK1

Stankevičiūtė

Vaitekūnas

Petkevičius

et al. 2016

Sci Rep

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Pyridinols and pyridinamines are important intermediates with many applications in chemical industry. The pyridine derivatives are in great demand as synthons for pharmaceutical products. Moreover, pyridines are used either as biologically active substances or as building blocks for polymers with unique physical properties. Application of enzymes or whole cells is an attractive strategy for preparation of hydroxylated pyridines since the methods for chemical synthesis of pyridinols, particularly aminopyridinols, are usually limited or inefficient. Burkholderia sp. MAK1 (DSM102049), capable of using pyridin-2-ol as the sole carbon and energy source, was isolated from soil. Whole cells of Burkholderia sp. MAK1 were confirmed to possess a good ability to convert different pyridin-2-amines and pyridin-2-ones into their 5-hydroxy derivatives. Moreover, several methylpyridines as well as methylated pyrazines were converted to appropriate N-oxides. In conclusion, regioselective oxyfunctionalization of pyridine derivatives using whole cells of Burkholderia sp. MAK1 is a promising method for the preparation of various pyridin-5-ols and pyridin-N-oxides.

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Microbial transformation of azaarenes and potential uses in pharmaceutical synthesis

Cited by 21 publications

References 121 publications

Green strategy from waste to value-added-chemical production: efficient biosynthesis of 6-hydroxy-3-succinoyl-pyridine by an engineered biocatalyst

Green strategy from waste to value-added-chemical production: efficient biosynthesis of 6-hydroxy-3-succinoyl-pyridine by an engineered biocatalyst

Biotransformations of organic compounds mediated by cultures of Aspergillus niger

Oxyfunctionalization of pyridine derivatives using whole cells of Burkholderia sp. MAK1

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