Synthesis of 1-deoxy-d-erythro-hexo-2,3-diulose, a major hexose Maillard intermediate

Glomb, Marcus A.; Pfahler, Christoph

doi:10.1016/s0008-6215(00)00219-6

Cited by 36 publications

(30 citation statements)

References 14 publications

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“…Hemodialysis was performed three times weekly for 4 -5 h using polysulfone dialyzers and dialysate containing bicarbonate buffer. (27), CML (28), N 6 -carboxyethyl lysine (CEL) (29), and N 6 -lactoyl lysine and N 6 -glycerinyl lysine (7) were synthesized according to the literature. The identities of target compounds was verified by nuclear magnetic resonance experiments.…”

Section: Methodsmentioning

confidence: 99%

Molecular Basis of Maillard Amide-Advanced Glycation End Product (AGE) Formation in Vivo

Henning¹,

Smuda²,

Girndt

et al. 2011

Journal of Biological Chemistry

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Background: Advanced glycation end products (AGEs) play a prominent role in various pathophysiologies. Results: A new class of lysine amide modifications was established in vivo. Conclusion: Non-enzymatic Maillard mechanisms participate on amide-AGE formation pathways in vivo. Significance: Plasma levels of the amide-AGEs were in the same range similar to other established lysine modifications and suggest a comparable impact of non-enzymatic biochemistry on pathophysiologies in the human organism.

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Section: Methodsmentioning

confidence: 99%

Molecular Basis of Maillard Amide-Advanced Glycation End Product (AGE) Formation in Vivo

Henning¹,

Smuda²,

Girndt

et al. 2011

Journal of Biological Chemistry

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“…The quinoxaline derivative of 1-deoxy-D-erythro-hexos-2,3-diulose (1-deoxyglucosone (1-DG)) was synthesized as described before [26].…”

Section: -Deoxy-d-threo-hexos-2-ulosementioning

confidence: 99%

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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“…Identification was achieved by NMR spectroscopy including 1 H, 13 C, distortionless enhancement by polarization transfer, homonuclear correlation spectroscopy, heteronuclear multiple-bond connectivity, and 1 H-detected heteronuclear multiple-quantum coherence experiments. All three substances showed similar signals in the 1 H and 13 C NMR spectra arising from the protons H-5Ј and H-8Ј and from the carbons C-4aЈ, C-5Ј, C-6Ј, C-7Ј, C-8Ј, and C-8aЈ of the quinoxaline skeletal structure (9,16,20,42). In contrast, Q1 to Q3 displayed clear differences in the carbohydrate backbone at C-2Ј and C-3Ј.…”

Section: Detection Of ␣-Dicarbonyl Compounds Derived From Fbpmentioning

confidence: 92%

Formation of 4-Hydroxy-2,5-Dimethyl-3[2H]-Furanone by Zygosaccharomyces rouxii : Identification of an Intermediate

Hauck

Brühlmann

Schwab

2003

Appl Environ Microbiol

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13 C]FBP to the nutrient medium revealed that only exogenously supplied FBP was transformed to HDMF (6). It was assumed that at least one metabolic step takes place in the cell wall or membrane of the yeast. However, the biosynthesis in plants and microorganisms is still unclear since no enzyme or intermediate involved in HDMF formation has been identified so far. Recently, the chemical formation of HDMF from FBP in the presence of NAD(P)H was reported (11). The authors proposed the dicarbonyl compound 1-deoxy-2,3-hexodiulose-6-phosphate as a possible intermediate which is subsequently reduced by NAD(P)H to the final product, HDMF. A similar biosynthetic pathway is anticipated in plants and microorganisms.Prior to the usage of Z. rouxii for the biotechnological production of the economically important flavor compound HDMF, it is of utmost significance to know the biosynthetic pathway of HDMF. The objective of this study was to obtain detailed information about HDMF formation from FBP by the yeast Z. rouxii. Here, we report on potential intermediates, such as ␣-dicarbonyls in the culture medium. Employment of the ␣-dicarbonyl-trapping reagent o-phenylenediamine revealed three highly reactive ␣-dicarbonyl structures derived from FBP in the nutrient medium. Structure elucidation of the corresponding quinoxaline derivatives demonstrated the chemical formation of the often postulated but never identified intermediate * Corresponding author. Present address: Biomolekulare Lebensmitteltechnologie,

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Synthesis of 1-deoxy-d-erythro-hexo-2,3-diulose, a major hexose Maillard intermediate

Cited by 36 publications

References 14 publications

Molecular Basis of Maillard Amide-Advanced Glycation End Product (AGE) Formation in Vivo

Molecular Basis of Maillard Amide-Advanced Glycation End Product (AGE) Formation in Vivo

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

Formation of 4-Hydroxy-2,5-Dimethyl-3[2H]-Furanone by Zygosaccharomyces rouxii : Identification of an Intermediate

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