Enzymatic synthesis of 2-keto-d-gluconate and 2-keto-d-galactonate from d-glucose and d-galactose with cell culture of Pseudomonas fluorescens and 2-keto-galactonate from d-galactono 1,4-lactone with partially purified 2-ketogalactonate reductase

Tanimura, Ritsuko; Hamada, A.; Ikehara, Kenji; Iwamoto, Ryoko

doi:10.1016/s1381-1177(03)00092-4

Cited by 17 publications

(10 citation statements)

References 11 publications

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“…A. niger Δ gaaC and T. reesei Δ lga1 convert D-galacturonate to 2-keto-3-deoxy-L-galactonate, which accumulates extracellularly. Production rates were comparable or better than those observed for similar products with bacterial cells [ 5 , 12 ] and could be further improved by optimising the provision of co-substrate for biomass and energy production. Total production, volumetric production rate and specific production rate were higher for A. niger Δ gaaC than T. reesei Δ lga1 and the ability of A. niger Δ gaaC to produce keto-deoxy-L-galactonate directly from pectin or polygalacturonate demonstrate that it is the more desirable production organism.…”

Section: Discussionmentioning

confidence: 84%

“…These rates were comparable or higher to those demonstrated for the production of 2-keto-D-galactonate from D-galactose (approx. 0.14 g l -1 h -1 ) by Pseudomonas fluorescens [ 5 ] and considerably higher than those observed for 2-keto-L-galactonate production by Erwinia herbicola (<0.2 mg l -1 h -1 ; [ 12 ].…”

Section: Discussionmentioning

confidence: 99%

“…Interest in galactonic acid derivatives has increased on account of the planar zigzag conformation they can adopt in solution [e.g. [ 2 , 4 ]], while keto sugars are useful intermediates in the production of various sugar derivatives [ 5 , 6 ]. Removal of water from L-galactonic acid leads to the formation of keto-deoxy-L-galactonic acid (3-deoxy-L- threo -hex-2-ulosonic acid).…”

Section: Introductionmentioning

confidence: 99%

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Bioconversion of D-galacturonate to keto-deoxy-L-galactonate (3-deoxy-L-threo-hex-2-ulosonate) using filamentous fungi

et al. 2010

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BackgroundThe D-galacturonic acid derived from plant pectin can be converted into a variety of other chemicals which have potential use as chelators, clarifiers, preservatives and plastic precursors. Among these is the deoxy-keto acid derived from L-galactonic acid, keto-deoxy-L-galactonic acid or 3-deoxy-L-threo-hex-2-ulosonic acid. The keto-deoxy sugars have been found to be useful precursors for producing further derivatives. Keto-deoxy-L-galactonate is a natural intermediate in the fungal D-galacturonate metabolic pathway, and thus keto-deoxy-L-galactonate can be produced in a simple biological conversion.ResultsKeto-deoxy-L-galactonate (3-deoxy-L-threo-hex-2-ulosonate) accumulated in the culture supernatant when Trichoderma reesei Δlga1 and Aspergillus niger ΔgaaC were grown in the presence of D-galacturonate. Keto-deoxy-L-galactonate accumulated even if no metabolisable carbon source was present in the culture supernatant, but was enhanced when D-xylose was provided as a carbon and energy source. Up to 10.5 g keto-deoxy-L-galactonate l-1 was produced from 20 g D-galacturonate l-1 and A. niger ΔgaaC produced 15.0 g keto-deoxy-L-galactonate l-1 from 20 g polygalacturonate l-1, at yields of 0.4 to 1.0 g keto-deoxy-L-galactonate [g D-galacturonate consumed]-1. Keto-deoxy-L-galactonate accumulated to concentrations of 12 to 16 g l-1 intracellularly in both producing organisms. This intracellular concentration was sustained throughout production in A. niger ΔgaaC, but decreased in T. reesei.ConclusionsBioconversion of D-galacturonate to keto-deoxy-L-galactonate was achieved with both A. niger ΔgaaC and T. reesei Δlga1, although production (titre, volumetric and specific rates) was better with A. niger than T. reesei. A. niger was also able to produce keto-deoxy-L-galactonate directly from pectin or polygalacturonate demonstrating the feasibility of simultaneous hydrolysis and bioconversion. Although keto-deoxy-L-galactonate accumulated intracellularly, concentrations above ~12 g l-1 were exported to the culture supernatant. Lysis may have contributed to the release of keto-deoxy-L-galactonate from T. reesei mycelia.

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Section: Discussionmentioning

confidence: 84%

Section: Discussionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Bioconversion of D-galacturonate to keto-deoxy-L-galactonate (3-deoxy-L-threo-hex-2-ulosonate) using filamentous fungi

et al. 2010

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“…This conversion can also be effected by a number of bacteria species, particularly by the genus Pseudomonas. [7][8][9][10] Similarly, the enzymatic oxidation of D-glucosone to D-arabino-hex-2-ulosonic acid has also been reported. 11 The acid is an important intermediate in the synthesis of D-erythro-hex-2-enono-1,4-lactone (D-erythorbic acid) 12 and isoascorbic acid.…”

Section: Introductionmentioning

confidence: 87%

A convenient synthesis of hexulosonic acids by IBX mediated oxidation of D-glucono-1,5-lactone derivatives

Kolender¹,

Puenzo²,

Varela³

2011

Arkivoc

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The oxidation of the free hydroxyl group of methyl 3,4:5,6-di-O-isopropylidene-D-gluconate 2 or its 2,3:5,6-di-O-isopropylidene analogue 3, the products of acetonation of D-glucono-1,5-lactone 1, has been attempted by alternative procedures. The oxidation of OH-2 in 2, or OH-4 in 3, with o-iodoxybenzoic acid (IBX) took place to afford the respective 2-keto 4 and 4-keto 7 derivatives in almost quantitative yields. In contrast, the oxidations with pyridinium dichromate were unsuccessful, and those using dimethylsulfoxide−acetic anhydride afforded low yields of 4 or 7. Selective removal of the isopropylidene groups in 4 or 7 with 88% aqueous acetic acid afforded, respectively, the methyl esters 5 or 8; whereas treatment with aqueous trifluoroacetic acid led to the free hexulosonic acids 6 or 9. The tautomeric preferences for the oxidation products 4 and 7, and their derivatives, have been established by 13 C NMR spectroscopy.

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“…For 2KGA preparation, at least three methods including chemical synthesis, enzymatic conversion, and microbial fermentation have been proposed. However, chemical and enzymatic methods had limits to large-scale production due to their critical reaction conditions, low yield and/or high process costs (Elseviers et al, 2000;Tanimura et al, 2003). Microbial fermentation is the main industrial 2KGA production method with two consecutive oxidations by glucose dehydrogenase and gluconate dehydrogenase.…”

Section: Introductionmentioning

confidence: 99%

Two-Stage Semi-Continuous 2-Keto-Gluconic Acid (2KGA) Production by Pseudomonas plecoglossicida JUIM01 From Rice Starch Hydrolyzate

Sun

Wang

Sun

et al. 2020

Front. Bioeng. Biotechnol.

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A two-stage semi-continuous strategy for producing 2-keto-gluconic acid (2KGA) by Pseudomonas plecoglossicida JUIM01 from rice starch hydrolyzate (RSH) has been developed. The initial glucose concentration (140 g/L) was selected for first-stage fermentation due to its highest 2KGA productivity of 7.58 g/(L • h), cell weight of 3.91 g/L, and residual glucose concentration of 25.00 g/L. Followed by removing 70.0% (v/v) of the first-stage broth and feeding 400.0 g/L of glucose to the secondstage fermentor, a total of 50680.0 g glucose was consumed, and 50005.20 g 2KGA was obtained with a yield of 0.9867 g/g by P. plecoglossicida JUIM01 after a 3-cycle two-stage semi-continuous fermentation. Our results indicated that the developed twostage semi-continuous fermentation could be industrially applied due to its high 2KGA concentration, 2KGA yield and operation efficiency.

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Enzymatic synthesis of 2-keto-d-gluconate and 2-keto-d-galactonate from d-glucose and d-galactose with cell culture of Pseudomonas fluorescens and 2-keto-galactonate from d-galactono 1,4-lactone with partially purified 2-ketogalactonate reductase

Cited by 17 publications

References 11 publications

Bioconversion of D-galacturonate to keto-deoxy-L-galactonate (3-deoxy-L-threo-hex-2-ulosonate) using filamentous fungi

Bioconversion of D-galacturonate to keto-deoxy-L-galactonate (3-deoxy-L-threo-hex-2-ulosonate) using filamentous fungi

A convenient synthesis of hexulosonic acids by IBX mediated oxidation of D-glucono-1,5-lactone derivatives

Two-Stage Semi-Continuous 2-Keto-Gluconic Acid (2KGA) Production by Pseudomonas plecoglossicida JUIM01 From Rice Starch Hydrolyzate

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