Enzymic oxidation of d-arabino-hexos-2-ulose (d-glucosone) to d-arabino-2-hexulosonic acid (“2-keto-d-gluconic acid”)

Geigert, John; Neidleman, Saul L.; Hirano, David S.; Wolf, Beverly; Panschar, Barbara M.

doi:10.1016/0008-6215(83)88229-9

Cited by 17 publications

(12 citation statements)

References 4 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The extent of sugar oxidation depends mainly on pH value, temperature, the type of sugar, and the presence and type of oxidising agents. Many papers reported on sugar oxidation proceeding under different conditions such as oxidation by enzymes (Geigert et al 1983), free oxygen (Samuelson & Thede 1968;Vuorinen 1985), hydrogen peroxide , or ozone (Marcq et al 2001), pyrolysis (Hodge 1967;Ponder & Richards 1993), γ-irradiation (Kawakishi et al 1975;Drijver & Holzapfel 1986), ultraviolet radiation (Phillips et al 1964), or sonolysis (Heusinger 1988).…”

mentioning

confidence: 99%

“…Yang and Montgomery (1996b) identified several C 4 , C 5 , and C 6 -saccharinic acids formed during the degradation of glucose and fructose in Ca(OH) 2 solution. Ulosonic (2-keto) acids are formed via aldos-2-uloses during, for example, oxidation of aldoses by HO • radicals (generated by the Fenton reagent, H 2 O 2 +Fe 2+ ) (Davídek et al 1990) or enzymatically (Geigert et al 1983).…”

mentioning

confidence: 99%

See 1 more Smart Citation

Formation of carboxylic acids during degradation of monosaccharides

Novotny¹,

Cejpek²,

Velı́šek³

2008

Czech J. Food Sci.

View full text Add to dashboard Cite

Novotný O., Cejpek K., Velíšek J. The formation of low molecular carboxylic and hydroxycarboxylic acids as well as sugar and deoxysugar acids from monosaccharides (d-glucose, d-fructose, d-arabinose, dl-glyceraldehyde, and 1,3-dihydroxyacetone) was studied in three different model systems: aqueous and alkaline solutions of potassium peroxodisulfate (K 2 S 2 O 8 ), and sodium hydroxide solution. In total, 3 low molecular carboxylic acids (formic, acetic and propionic), 24 hydroxycarboxylic acids, and 12 corresponding lactones were identified and quantified by GC/MS. Formic, acetic, and propionic acids were isolated by extraction with diethyl ether and directly analysed by GC/MS; hydroxycarboxylic acids and their lactones were monitored as their trimethylsilylated derivatives using the same method. Formic, acetic, l-lactic, glycollic, dl-2,4-dihydroxybutanoic acids and aldonic acids derived from the parent sugars were the most abundant compounds in all model systems. Within the models investigated, the yield of carboxylic acids and hydroxycarboxylic acids (together with their lactones) ranged between 9.3-22.2% (n/n) and between 3.6-116.9% (n/n), respectively. The amount of acids was significantly lower in aqueous solutions of K 2 S 2 O 8 than in the alkaline solutions. The data obtained indicate that lower carboxylic acids are formed by both subsequent reactions (oxidation and/or intramolecular Cannizzaro reaction) of the sugar fragmentation products and direct decomposition of some intermediates such as uloses or hydroperoxides derived from the parent sugars. The acids possessing the original sugar skeleton are formed as a result of sugar oxidation or benzilic acid type rearrangement of deoxyuloses. Lower acids may also be formed by a recombination of free radicals.

show abstract

mentioning

confidence: 99%

mentioning

confidence: 99%

Formation of carboxylic acids during degradation of monosaccharides

Novotny¹,

Cejpek²,

Velı́šek³

2008

Czech J. Food Sci.

View full text Add to dashboard Cite

show abstract

“…The 13 C NMR (100 MHz) spectra of 2/5-kGA crystals were obtained using a Bruker Avance III HD 600 MHz spectrometer equipped with a 5 mm BBO probe using a combined pulse proton decoupling sequence. 100 mg of dried 2-kGA was dissolved in 0.5 mL of D 2 O-d2.…”

Section: Nmr Analysismentioning

confidence: 99%

“…10–12 Both chemical and enzymatic methods employ glucose as the substrate to generate 2- and 5-kGA using a metal catalyst or oxidase (pyranose-2-oxidase, glucose-1-oxidase, glucose-2-oxidase), but the process forms GA, H 2 O 2 and other by-products that seriously affect the quality of the product. 13,14 Fermentation and cell catalysis are more economically competitive compared with the chemical and enzymatic methods, so these two technologies are usually applied in industry to prepare 2- and 5-kGA. At present, microorganisms that produce 2- and 5-kGA include Pseudomonas fluorescens , G. oxydans , Serratia marcescens , Arthrobacter globiformis and Pseudomonas aeruginosa.…”

Section: Introductionmentioning

confidence: 99%

Cascading and precise regulation of the selective bio-production of 2- or 5-ketogluconic acid from glucose with whole-cell catalysis technology

et al. 2023

View full text Add to dashboard Cite

show abstract

“…[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. 13 Moreover, ester derivatives (D-arabino-hex-2-ulopyranosonates)…”

Section: Introductionmentioning

confidence: 99%

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

Kolender¹,

Puenzo²,

Varela³

2011

Arkivoc

View full text Add to dashboard Cite

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.

show abstract

Enzymic oxidation of d-arabino-hexos-2-ulose (d-glucosone) to d-arabino-2-hexulosonic acid (“2-keto-d-gluconic acid”)

Cited by 17 publications

References 4 publications

Formation of carboxylic acids during degradation of monosaccharides

Formation of carboxylic acids during degradation of monosaccharides

Cascading and precise regulation of the selective bio-production of 2- or 5-ketogluconic acid from glucose with whole-cell catalysis technology

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

Contact Info

Product

Resources

About