Formation of 1-deoxy-d-erythro-2,3-hexodiulose from Amadori compounds

Beck, Jakob; Ledl, Franz; Severin, Theodor

doi:10.1016/0008-6215(88)85058-4

Cited by 57 publications

(26 citation statements)

References 6 publications

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“…1a) [24,[27][28][29]. In contrast to their parent compounds, the latter show specific maxima of UV absorption at 316 nm for saturated and 335 nm for unsaturated quinoxalines.…”

Section: Resultsmentioning

confidence: 93%

Identification and quantification of six major α-dicarbonyl process contaminants in high-fructose corn syrup

et al. 2012

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High-fructose corn syrup (HFCS) is a widely used liquid sweetener produced from corn starch by hydrolysis and partial isomerization of glucose to fructose. During these processing steps, sugars can be considerably degraded, leading, for example, to the formation of reactive α-dicarbonyl compounds (α-DCs). The present study performed targeted screening to identify the major α-DCs in HFCS. For this purpose, α-DCs were selectively converted with o-phenylendiamine to the corresponding quinoxaline derivatives, which were analyzed by liquid chromatography with hyphenated diode array-tandem mass spectrometry (LC-DAD-MS/MS) detection. 3-Deoxy-D-erythro-hexos-2-ulose (3-deoxyglucosone), D-lyxo-hexos-2-ulose (glucosone), 3-deoxy-D-threo-hexos-2-ulose (3-deoxygalactosone), 1-deoxy-D-erythro-hexos-2,3-diulose (1-deoxyglucosone), 3,4-dideoxyglucosone-3-ene, methylglyoxal, and glyoxal were identified by enhanced mass spectra as well as MS/MS product ion spectra using the synthesized standards as reference. Addition of diethylene triamine pentaacetic acid and adjustment of the derivatization conditions ensured complete derivatization without de novo formation for all identified α-DCs in HFCS matrix except for glyoxal. Subsequently, a ultra-high performance LC-DAD-MS/MS method was established to quantify 3-deoxyglucosone, glucosone, 3-deoxygalactosone, 1-deoxyglucosone, 3,4-dideoxyglucosone-3-ene, and methylglyoxal in HFCS. Depending on the α-DC compound and concentration, the recovery ranged between 89.2% and 105.8% with a relative standard deviation between 1.9% and 6.5%. Subsequently, the α-DC profiles of 14 commercial HFCS samples were recorded. 3-Deoxyglucosone was identified as the major α-DC with concentrations up to 730 μg/mL HFCS. The total α-DC content ranged from 293 μg/mL to 1,130 μg/mL HFCS. Significantly different α-DC levels were not detected between different HFCS specifications, but between samples of various manufacturers indicating that the α-DC load is influenced by the production procedures.

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“…1a) [24,[27][28][29]. In contrast to their parent compounds, the latter show specific maxima of UV absorption at 316 nm for saturated and 335 nm for unsaturated quinoxalines.…”

Section: Resultsmentioning

confidence: 93%

Identification and quantification of six major α-dicarbonyl process contaminants in high-fructose corn syrup

et al. 2012

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“…A similar finding has also been reported by Martins and Van Boekel (2005) in Glu-Gly MR model systems. It is important to note that under neutral and alkaline conditions, Amadori products undergo 2,3-enolization to produce 2,3-enediols, which are further degraded into 1-deoxyosones (Beck et al, 1988;Obrien & Morrissey, 1989). The β cleavage of 1-DG or 1-deoxypentosone (1-DP) in hexose or pentose MR systems, respectively, results in the production of acetic acid, leading to the decrease of pH (Davidek, Devaud, Robert, & Blank, 2005;Davidek, Gouezec, Devaud, & Blank, 2008).…”

Section: Resultsmentioning

confidence: 99%

“…These intermediate MRPs undergo further degradation to 3-or 1-deoxyosones after the loss of amino acid (Beck, Ledl, & Severin, 1988;Obrien & Morrissey, 1989). The reactive α-dicarbonyl compounds containing the original carbon backbone are further fragmented to form C2, C3, C4, and C5 carbonyl compounds (Gobert & Glomb, 2009;Hofmann, 1999).…”

Section: Resultsmentioning

confidence: 99%

Identification and quantification of α-dicarbonyl compounds produced in different sugar-amino acid Maillard reaction model systems

Chen

Kitts

2011

Food Research International

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“…glucose, lactose or maltose. However, the unstable 1-deoxyosone (1DG) is more often reported to be the key intermediate of the advanced stage of nonenzymatic glycosylation when disaccharides having a 1, 4 glycosidic bond react in systems at neutral or alkaline pH values [2,7]. Formation of this dicarbonyl intermediate does not need breakage of the glycosidic bond at C4 [4] and, contrary to 3DG, this carbon atom is not involved in further condensation reactions leading to five-or six-membered rings.…”

Section: Introductionmentioning

confidence: 99%

Formation of protein bound lysine-derived galactosyl and glucosyl pyrroles in heated model systems

Pellegrino

Noni

Cattaneo

2000

Nahrung

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Residues of lysine-substituted AGEs (advanced glycosylation end-products) arising from the Maillard reaction and containing the carbon backbone of lactose or maltose, thus deriving from 1-desoxy-ketose degradation, were produced when casein was heated in the presence of the corresponding U14C labelled disaccharides. The enzymatic hydrolysates of the washed casein were purified by SPE and submitted to HPLC on a C18 column flushed with diluted acetic acid. A specific chromatographic peak (lambda max, 288.1 nm; MW, 416.2 Da) with a different retention time was obtained for each disaccharide reacted. On the basis of the value of the specific radioactivity, the two compounds appeared to contain the whole carbon backbone of the parent sugar. Analyses by MS/MS and NMR performed on the same two compounds extracted at preparative scale from lysine-lactose and lysine-maltose model systems allowed the structure assignment of 6-[2-acetyl-3-(beta-D-galactopyranosyloxy)-1-pyrrolyl] 2-amino hexanoic acid and 6-[2-acetyl-3-(alpha-D-glucopyranosyloxy)-1-pyrrolyl] 2-amino hexanoic acid, respectively. Both compounds submitted to enzymatic deglycosylation by specific alpha- or beta-glucosidases produced the lysine-derived acetyl pyrrole 6-(2-acetyl-3-hydroxy-1-pyrrolyl) 2-amino hexanoic acid (lambda max, 288.1 nm; MW, 254.1 Da). Galactosyl- and glucosyl-isomaltoles, extracted from the lysine-containing systems, identified with the reference molecules and heated in the presence of lysine under slightly alkaline conditions, gave the expected lysine-derived glycosyl pyrroles as identified above. The HPLC conditions were optimized by adjusting the composition of the eluting solvent and temperature of the column to achieve the best separation and identification of the AGEs in mixtures such as foods with possible interfering molecules like Trp and lysyl pyrrole aldehyde. Because of the reported presence of the two precursors isomaltol glycosydes in some foods, the corresponding lysine-derived glycosyl pyrroles can occur as both protein bound and in free form.

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Formation of 1-deoxy-d-erythro-2,3-hexodiulose from Amadori compounds

Cited by 57 publications

References 6 publications

Identification and quantification of six major α-dicarbonyl process contaminants in high-fructose corn syrup

Identification and quantification of six major α-dicarbonyl process contaminants in high-fructose corn syrup

Identification and quantification of α-dicarbonyl compounds produced in different sugar-amino acid Maillard reaction model systems

Formation of protein bound lysine-derived galactosyl and glucosyl pyrroles in heated model systems

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