Enzymatic Reduction of 9-Methoxytariacuripyrone by Saccharomyces cerevisiae and Its Antimycobacterial Activity

Álvarez-Fitz, Patricia; Álvarez, Laura; Marquina, Silvia; Luna-Herrera, Julieta; Navarro-García, Víctor Manuel

doi:10.3390/molecules17078464

Cited by 12 publications

(3 citation statements)

References 21 publications

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“…Nitroalkenes 34 gave the nitroalkanes 35 with ee values ranging between 66 and 98% and yields between 20 and 60% [173,174]. 9-Methoxytariacuripyrone 36 was reduced by baker's yeast [175] to yield 5-amino-9-methoxy-3,4-dihydro-2H-benzo[h]chromen-2-one 37 being highly active as an antituberculosis agent.…”

Section: Figure 2110mentioning

confidence: 99%

Yeast‐Mediated Stereoselective Synthesis

Csük

2016

Green Biocatalysis

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Section: Figure 2110mentioning

confidence: 99%

Yeast‐Mediated Stereoselective Synthesis

Csük

2016

Green Biocatalysis

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“…Biotransformation is a powerful tool for obtaining valuable products in industrial processes [1,2]. The most impressive advantage of biotransformation over other traditional synthesis techniques is the respective enzyme's selectivity, which enantiomerically generates pure products and reduces the cost of purification.…”

Section: Introductionmentioning

confidence: 99%

Aspergillus sclerotiorum Whole-Cell Biocatalysis: A Sustainable Approach to Produce 3-Hydroxy-phenazine 1-Carboxylic Acid from Phenazine 1-Carboxylic Acid

et al. 2023

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In green chemistry, filamentous fungi are regarded as a kind of robust microorganism for the biotransformation of natural products. Nonetheless, the screening of microorganisms is crucial for the effective biotransformation of natural products, such as phenazine compounds. The precursor metabolite of most phenazine derivatives in Pseudomonas spp. is phenazine-1-carboxylic acid (PCA), the key constituent of shenqinmycin, widely used to control rice sheath blight in southern China. In this study, a new fungus strain Aspergillus sclerotiorum was isolated, which can efficiently convert PCA into 3-hydroxy-phenazine 1-carboxylic acid (3-OH-PCA). Moreover, an effective whole cells biotransformation system was designed by screening optimal reaction conditions and carbon sources. Hence, Aspergillus sclerotiorum exhibited desirable adaptation by the consumption of different carbon sources and maximum whole-cell biomass (10.6 g/L DCW) was obtained as a biocatalyst from glucose. Optimal conditions for whole-cell biocatalysis of PCA were evaluated, including a PCA concentration of 1120 mg/L, a pH of 7.0, a temperature of 25 °C, a rotation rate of 200 rpm, and dry cell weight of 15 g/L for 60 h; thus, 1060 mg/L of 3-OH-PCA was obtained and the conversion efficiency of PCA was 94%. Hence, the results of the repeated batch mood revealed that the biotransformation efficiency of fungus pellets reduced with each subsequent cycle, but remained stable in all five cycles with the provision of a glucose supplement. These findings present the prospect of using filamentous fungi for the whole-cell biocatalysis of phenazine in enormous amounts and the efficient production of 3-OH-PCA. Moreover, these results laid the foundation for further research to disclose the genetic-based mechanism of the strain responsible for PCA biotransformation.

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“…Naphthalenamines and their derivatives are an important class of compounds due to their biological activity, which includes emetic, spasmolytic, and antimicrobacterial activity; they are also known for their utility as starting materials for azo dyes . Moreover, their homo- and heterodimers [i.e., 1,1′-binaphthyl-2,2′-amines (BINAMs)] have recently received considerable attention as axially chiral ligands, organocatalysts, and reagents .…”

Section: Introductionmentioning

confidence: 99%

Palladium(II)-Catalyzed Annulation of Alkynes with 2-(Cyanomethyl)phenylboronates Leading to 3,4-Disubstituted 2-Naphthalenamines

2015

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1,2-Bis(diphenylphosphino)ethane (dppe)-ligated palladium(II) complexes catalyze the annulation of internal alkynes with 2-(cyanomethyl)phenylboronates to provide 3,4-disubstituted-2-naphthalenamines in good yields. The annulation reaction proceeds under mild and neutral conditions and requires methanol as an essential solvent. In addition to symmetrical alkynes, unsymmetrical alkynes substituted by aryl, alkyl, and alkynyl groups participate in the annulation to afford the corresponding 2-naphthalenamines with electron-withdrawing sp(2)- and sp-carbons preferentially located at the C-3 position. Substituents including an alkyl or alkoxy group on the cyanomethyl moiety and a halogen atom on the benzene ring in the boronates are compatible with the reaction conditions. The annulation proceeds through the transmetalation of the palladium(II) complexes with the boronates and alkyne insertion followed by nucleophilic addition of the generated alkenylpalladium(II) species to the intramolecular cyano group. Stoichiometric reactions revealed that the methanol solvent was effective for both transmetalation and catalyst regeneration.

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Enzymatic Reduction of 9-Methoxytariacuripyrone by Saccharomyces cerevisiae and Its Antimycobacterial Activity

Cited by 12 publications

References 21 publications

Yeast‐Mediated Stereoselective Synthesis

Yeast‐Mediated Stereoselective Synthesis

Aspergillus sclerotiorum Whole-Cell Biocatalysis: A Sustainable Approach to Produce 3-Hydroxy-phenazine 1-Carboxylic Acid from Phenazine 1-Carboxylic Acid

Palladium(II)-Catalyzed Annulation of Alkynes with 2-(Cyanomethyl)phenylboronates Leading to 3,4-Disubstituted 2-Naphthalenamines

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