Recent Trends in the Chemistry of Pyridine N‐Oxides

Youssif, Shaker

doi:10.1002/chin.200302270

Cited by 6 publications

(13 citation statements)

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“…PY, widely used as industrial solvent and starting compound in diverse chemical syntheses [8], is the simplest six-membered N-heterocycle and a rather unactivated, aromatic molecule that is chemically difficult to oxygenate, especially at the N-position [9]. There are a few PY-utilizing bacteria (e.g.…”

Section: Introductionmentioning

confidence: 99%

“…The chemistry and applications of PY N-oxides have received more and more attention over the last two decades due to their usefulness as synthetic intermediates and their biological importance [8,9,13]. There are several chemical methods to achieve PY N-oxidation/oxygenation including ring transformations, oxidation by peracids or metallo-organic oxidants and cycloaddition [9].…”

Section: Introductionmentioning

confidence: 99%

“…There are several chemical methods to achieve PY N-oxidation/oxygenation including ring transformations, oxidation by peracids or metallo-organic oxidants and cycloaddition [9]. All these reactions, however, are relatively unspecific and elaborate.…”

Section: Introductionmentioning

confidence: 99%

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Pyridine as novel substrate for regioselective oxygenation with aromatic peroxygenase from Agrocybe aegerita

et al. 2008

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Agrocybe aegerita peroxidase (AaP) is a versatile extracellular biocatalyst that can oxygenate aromatic compounds. Here, we report on the selective oxidation of pyridine (PY) yielding pyridine N-oxide as sole product. Using H 2 18 O 2 as co-substrate, the origin of oxygen was confirmed to be the peroxide. Therefore, AaP can be regarded as a true peroxygenase transferring one oxygen atom from peroxide to the substrate. To our best knowledge, there are only two types of enzymes oxidizing PY at the nitrogen: bacterial methane monooxygenase and a few P450 monooxygenases. AaP is the first extracellular enzyme and the first peroxidase that catalyzes this reaction, and it converted also substituted PYs into the corresponding N-oxides.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Pyridine as novel substrate for regioselective oxygenation with aromatic peroxygenase from Agrocybe aegerita

et al. 2008

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“…HSP, which has a hydroxyl group and a side-chain, is a promising precursor for the synthesis of 2,5-di-substituted and 2,3,5-tri-substituted pyridine derivatives1314. These 2,5-/2,3,5-substituted pyridine units are also present in several currently marketed drugs, including pioglitazone (Actos, for diabetes), eszopiclone (Lunesta, for insomnia), and the recently approved crizotinib (Xalkori, for cancer)15.…”

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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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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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“…Ketones and aldehydes undergo oxygen insertion reaction (Baeyer-Villiger oxidation) [69,70]. Peroxyacetic acid was applied for N-oxidation of tertiary amines and the pyridine-like heteroaromatic nitrogen atom [71]. The reaction proceeded in high temperature.…”

Section: Hydroperoxides In Acidic Mediamentioning

confidence: 99%

Non-Metal and Enzymatic Catalysts for Hydroperoxide Oxidation of Organic Compounds

Młochowski¹

2011

TOCATJ

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Oxidation of different groups of organic compounds, with hydroperoxides catalyzed by non-heavy metal containing low-molecular-weight compounds and enzymes is reviewed. This article is concentrated mainly on the hydrogen peroxide and tert-butyl hydroperoxide, however other less common hydroperoxides are also mentioned. Since hydroperoxides themselves are inactive toward most of the organic substrates, in situ activation of the oxidant is necessary. For this purpose various activators have been applied in stoichiometric or catalytic amounts. The carboxylic acids, nitriles, amides and urea are representative for the first category. The organocatalysts such as-halo carbonyl compounds, ketones, imines, iminium salts, nitroxyl radicals and polyaminoacids, selenium compounds and enzymes are presented. They are involved in oxygen, and electron transfer processes whose mechanisms are briefly discussed, and their applications in laboratory and industrial synthesis are indicated.

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Recent Trends in the Chemistry of Pyridine N‐Oxides

Cited by 6 publications

References 0 publications

Pyridine as novel substrate for regioselective oxygenation with aromatic peroxygenase from Agrocybe aegerita

Pyridine as novel substrate for regioselective oxygenation with aromatic peroxygenase from Agrocybe aegerita

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

Non-Metal and Enzymatic Catalysts for Hydroperoxide Oxidation of Organic Compounds

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