Monosaccharide–H2O2 reactions as a source of glycolate and their stimulation by hydroxyl radicals

Maksimović, Vuk; Mojović, Miloš; Vučinić, Željko

doi:10.1016/j.carres.2006.06.023

Cited by 18 publications

(12 citation statements)

References 39 publications

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“…Moreover, the complete elimination of H 2 O 2 avoids enzyme inactivation by chemical oxidation and, importantly, avoids the unspecific oxidation of DHA that reduces the product yield of the biotransformation dramatically. [24] The action of both NOX and CAT recycles and eliminates the redox cofactor and the peroxide in situ, respectively, within the same porous microenvironment, which increases both the kinetics and yield of the DHA biosynthesis.…”

Section: Resultsmentioning

confidence: 99%

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Immobilizing Systems Biocatalysis for the Selective Oxidation of Glycerol Coupled to In Situ Cofactor Recycling and Hydrogen Peroxide Elimination

et al. 2015

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The combination of three different enzymes immobilized rationally on the same heterofunctional carrier allowed the selective oxidation of glycerol to 1,3‐dihydroxyacetone (DHA) coupled to in situ redox‐cofactor recycling and H2O2 elimination. In this cascade, engineered glycerol dehydrogenase with reduced product inhibition oxidized glycerol selectively to DHA with the concomitant reduction of NAD+ to NADH. NADH oxidase regenerated the NAD+ pool by oxidizing NADH to NAD+ to form H2O2 as the byproduct. Finally, catalase eliminated H2O2 to yield water and O2 as innocuous products, which avoided the spontaneous DHA oxidation triggered by H2O2. The co‐immobilization of the three enzymes on the same porous carrier allowed the in situ recycling and disproportionation of the redox cofactor and H2O2, respectively, to produce up to 9.5 mM DHA, which is 18‐ and 6‐fold higher than glycerol dehydrogenase itself and a soluble multienzyme system, respectively.

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Section: Resultsmentioning

confidence: 99%

“…[23] The in situ elimination of H 2 O 2 avoids the spontaneous oxidation of DHA to glycolic acid, which reduces the final product yield. [24] Finally, the three enzymes were compatible in potassium phosphate buffer at pH 7, hence it is possible to perform this biotransformation in one pot and in aqueous media.…”

Section: Resultsmentioning

confidence: 99%

Immobilizing Systems Biocatalysis for the Selective Oxidation of Glycerol Coupled to In Situ Cofactor Recycling and Hydrogen Peroxide Elimination

et al. 2015

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“…High Pressure Liquid Chromatography (HPLC) analyses of carbohydrates were performed according to Maksimović et al (2006), using a Waters Breeze chromatographic system (Waters, Milford, MA) connected to a Waters 2465 electrochemical detector with a 3 mm gold working electrode and a hydrogen referent electrode. Separation of sugars was performed on CarboPac PA1 (Dionex, Sunnyvale, CA) 250 9 4 mm column equipped with corresponding CarboPac PA1 guard column using 0.2 M NaOH as a mobile phase.…”

Section: Carbohydrates Analysesmentioning

confidence: 99%

Contribution of inorganic cations and organic compounds to osmotic adjustment in root cultures of two Centaurium species differing in tolerance to salt stress

Mišić

Šiler

Živković

et al. 2011

Plant Cell Tiss Organ Cult

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The effect of reduced availability of sugars on growth and essential metabolic processes in roots, resulting from decreased photosynthesis under salinity, was excluded by establishing a non-photosynthetic model-system in this study: root cultures of Centaurium maritimum (L.) Fritch and Centaurium spicatum (L.) Fritch. The contribution of inorganic cations and organic compounds (e.g. carbohydrates and amino acids) to the osmotic adjustment (OA) in roots during short-term exposure to various salt concentrations (0, 50, 100 or 200 mM NaCl) was emphasized. Observed morphological and histological changes in roots were species specific, and were dependent on salinity level. Although C. spicatum appears to be more tolerant to salt stress, both species employed similar strategies in response to elevated salinity to different extents, and displayed effective OA mechanisms. Under low and moderate salinity, inorganic cations were the major contributors to OA in roots of both species, followed by soluble sugars, while the relative contribution of proline (Pro) and free amino acids was insignificant. Osmotic adjustment under severe stress appears to be mediated by increased accumulation of organic compounds. The analysis of the intraspecies variability in salt response of C. spicatum and C. maritimum roots enabled the identification of some organic compounds which could be used as potential biochemical markers in screening for salt tolerance, including Pro in C. spicatum, and trehalose and polyols in C. maritimum.

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“…Dihydroxyacetone 3 mM at pH 8 in 30 min was also oxidized by these Fenton free radicals more readily than fructose at pH 4 to form glycolic acid (from both likely via a glycolaldehyde intermediate). Also formed was formate (from both), hydroxyl radicals (from dihydroxyacetone), and ribose (from fructose) (Maksimovic et al, 2006). Furthermore, 60% of 3 mM glucose was oxidized by Fenton radicals at pH 5 in less than 3 h to eight identified products including arabonic and gluconic acids (Buriova et al, 2004).…”

Section: Discussionmentioning

confidence: 98%

Hepatocyte inflammation model for cytotoxicity research: fructose or glycolaldehyde as a source of endogenous toxins

Feng

Wong

Dong³

et al. 2009

Archives of Physiology and Biochemistry

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Insulin resistance and hepatotoxicity induced in high fructose fed rats may involve fructose derived endogenous toxins formed by inflammation. Thus fructose was seventy-fold more toxic if hepatocytes were exposed to non-toxic levels of hydrogen peroxide (H(2)O(2)) released by inflammatory cells. This was prevented by iron (Fe) chelators, hydroxyl radical scavengers, and increased by Fe, copper (Cu) or catalase inhibition. Fructose or glyceraldehyde/dihydroxyacetone metabolites were oxidized by Fenton radicals to glyoxal. Glyoxal (15 microM) cytotoxicity was increased about 200-fold by H(2)O(2). Glycolaldehyde was enzymically formed from glyceraldehyde, the fructokinase/aldolase B product of fructose. Glycolaldehyde cytotoxicity was increased 20-fold by H(2)O(2). The oxidative stress cytotoxicity induced was attributed to the Fenton oxidation of glycolaldehyde forming glycolaldehyde radicals and glyoxal, since cytotoxicity was prevented by aminoguanidine (glyoxal trap) or Fenton inhibitors. Glyoxal was also the Fenton product responsible for glycolaldehyde protein carbonylation as carbonylation was prevented by aminoguanidine or Fenton inhibitors.

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Monosaccharide–H2O2 reactions as a source of glycolate and their stimulation by hydroxyl radicals

Cited by 18 publications

References 39 publications

Immobilizing Systems Biocatalysis for the Selective Oxidation of Glycerol Coupled to In Situ Cofactor Recycling and Hydrogen Peroxide Elimination

Immobilizing Systems Biocatalysis for the Selective Oxidation of Glycerol Coupled to In Situ Cofactor Recycling and Hydrogen Peroxide Elimination

Contribution of inorganic cations and organic compounds to osmotic adjustment in root cultures of two Centaurium species differing in tolerance to salt stress

Hepatocyte inflammation model for cytotoxicity research: fructose or glycolaldehyde as a source of endogenous toxins

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