Regioselective reduction of substituted dinitroarenes using baker's yeast

Davey, C. L.; Powell, Lawson W.; Turner, Nicholas J.; Wells, Andrew S.

doi:10.1016/0040-4039(94)80139-8

Cited by 22 publications

(6 citation statements)

References 6 publications

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“…Other reagents such as NaBH 4 −Pd/C and H 3 PO 2 −Pd/C gave bad results. An attempt of reduction in the presence of bakers' yeast also failed. Finally the best result was obtained with SnCl 2 ·2H 2 O 13a,19 in ethanol.…”

Section: Resultsmentioning

confidence: 99%

Synthesis of Norcarbovir Analogues, the First Examples of Cyclobutene Nucleosides Unsubstituted at the Vinylic Position

Gourdel-Martin

Huet

1997

J. Org. Chem.

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Two cyclobutene nucleosides, 27 and 29, analogous to the yet unknown norcarbovir, and with adenine and hypoxanthine as the base moieties, respectively, were synthesized starting from cis-3-cyclobutene-1,2-dicarboxylic anhydride (6). Its reduction to lactone 9 followed by reaction with ammonia and then Hofmann rearrangement led to cyclic carbamate 15 which was the key intermediate of these syntheses. Its tert-butoxycarbonyl derivative 17 led to the ring opening of the heterocyclic moiety at low temperature. Compound 18 was thus obtained, and the successive benzylation and then treatment with hydrochloric acid yielded hydrochloride 21. Construction of bases was achieved in satisfying overall yields provided that mild experimental conditions from 21 to 27 or 29 were used to restrict the unwanted electrocyclic ring opening. Nitropyrimidine 31 was also prepared from 21 via the intermediate 23.

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Section: Resultsmentioning

confidence: 99%

Synthesis of Norcarbovir Analogues, the First Examples of Cyclobutene Nucleosides Unsubstituted at the Vinylic Position

Gourdel-Martin

Huet

1997

J. Org. Chem.

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“…2 This metabolic activity is widespread among bacteria, 3 fungi, plants, 4 and yeasts. 5 The enzymes responsible for these reductive biotransformations are flavoproteins from the Old Yellow Enzyme (OYE) family. 6 In the context of these studies, xenobiotic reductases XenA and XenB from Pseudomonas sp.…”

Section: Introductionmentioning

confidence: 99%

Reductive biotransformation of nitroalkenes via nitroso-intermediates to oxazetes catalyzed by xenobiotic reductase A (XenA)

et al. 2011

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A novel reductive biotransformation pathway for β,β-disubstituted nitroalkenes catalyzed by flavoproteins from the Old Yellow Enzyme (OYE) family was elucidated. It was shown to proceed via enzymatic reduction of the nitro-moiety to furnish the corresponding nitroso-alkene, which underwent spontaneous (non-enzymatic) electrocyclization to form highly strained 1,2-oxazete derivatives. At elevated temperatures the latter lost HCN via a retro-[2 + 2]-cycloaddition to form the corresponding ketones. This pathway was particularly dominant using xenobiotic reductase A, while pentaerythritol tetranitrate-reductase predominantly catalyzed the biodegradation via the Nef-pathway.

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“…After removal of the organic solvent by vacuum evaporation, the residue was dissolved again in a proper volume of ethyl acetate and was purified by silica flash chromatography in n-hexane:ethyl acetate (5:1 v/v) to give pure hydroxylamine with a conversion yield of 75%. The structure and the molecular weight of the 4-HANA were verified by 1 H NMR, 13 C NMR and LC-MS, respectively.…”

Section: Synthesis Of 4-anamentioning

confidence: 99%

“…The crude product was purified by silica gel chromatography in n-hexane:ethyl acetate (10:1, v/v). The structure and the molecular weight of the pure 4-ANA were verified by 1 H NMR, 13 C NMR and LC-MS, respectively, and its purity was checked by RP-HPLC. [76,77] and recently as biocatalysts for aromatic nitroreduction [78].…”

Section: Synthesis Of 4-anamentioning

confidence: 99%

“…Microorganisms possessing the ability to reduce a wide range of nitroarene compounds are known [1,2] and have become valuable assets in biodegradation of nitro explosives [3][4][5][6][7][8][9], bioremediation of other nitroaromatic pollutants [10,11], and in biotransformation processes [12][13][14][15][16][17][18]. Nitroarenes, arylhydroxylamines and arylamines are important intermediates in the industrial manufacturing of dyes, pesticides and plastics, and are significant environmental pollutants.…”

Section: Introductionmentioning

confidence: 99%

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Assessment of 4-nitro-1,8-naphthalic anhydride reductase activity in homogenates of bakers’ yeast by reversed-phase high-performance liquid chromatography

Yang

Qian

et al. 2007

Journal of Chromatography B

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Regioselective reduction of substituted dinitroarenes using baker's yeast

Cited by 22 publications

References 6 publications

Synthesis of Norcarbovir Analogues, the First Examples of Cyclobutene Nucleosides Unsubstituted at the Vinylic Position

Synthesis of Norcarbovir Analogues, the First Examples of Cyclobutene Nucleosides Unsubstituted at the Vinylic Position

Reductive biotransformation of nitroalkenes via nitroso-intermediates to oxazetes catalyzed by xenobiotic reductase A (XenA)

Assessment of 4-nitro-1,8-naphthalic anhydride reductase activity in homogenates of bakers’ yeast by reversed-phase high-performance liquid chromatography

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