Study on the decomposition of the amadori compoundN-(1-deoxy-D-fructos-1-y1)-glycine in model systems: Quantification by fast atom bombardment tandem mass spectrometry

Staempfli, Andreas; Blank, Imre; Fumeaux, René; Fay, Laurent B.

doi:10.1002/bms.1200231007

Cited by 34 publications

(22 citation statements)

References 14 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…5a) which is (1 cm , b), allysine-(1 allysine , c), and para-tyrosinecontaining peptide (1 Ypara , d) in phosphate buffer (pH 7.4) in iron absence (square), or in the presence of low (triangle) or high iron (diamond) with (dots) or without ascorbate (lines), respectively significantly faster than reported for N-glycated amino acids. For example, 5 % or more of N-(1-deoxy-d-fructos-1-yl)glycine remained when incubated at 90-100 °C for 1.5 h (Staempfli et al 1994;Davidek et al 2002;. N-terminally glycated peptides were studied only up to 70 °C, but showed an even slower degradation behavior (Jakas and Horvat 2003), which could be attributed to either the lower temperature and the lower concentration of catalytically active phosphate buffer or their generally higher stability.…”

Section: Discussionmentioning

confidence: 98%

Oxidative degradation of N ε-fructosylamine-substituted peptides in heated aqueous systems

2015

View full text Add to dashboard Cite

Glycation, or non-enzymatic glycosylation, is a common protein modification formed by reactions between reducing sugars (i.e. aldoses and ketoses) with protein amino groups. Resulting Amadori and Heyns compounds, respectively, can be oxidatively degraded yielding a structurally heterogeneous group of advanced glycation end-products. We have studied this process in aqueous conditions at 95 °C in terms of appearing products and their formation kinetics in the presence or absence of reactive oxygen species (ROS)-generating systems (iron(II) sulfate). RP-HPLC-ESI-MS revealed 20 products, 12 of which were confirmed after synthesis by identical retention times and fragmentation patterns. These products accumulated during the incubation period of 4 h (N(ε)-carboxymethyl-, N(ε)-formyl- and N(ε)-methyl lysine) or appeared intermediately (2-aminoadipic semialdehyde, N(ε)-ethanalyl lysine). Acidic and basic amino acid residues near the glycation site and elevated ROS levels in the reaction mixture had significant effects on both product formation and degradation kinetics.

show abstract

Section: Discussionmentioning

confidence: 98%

Oxidative degradation of N ε-fructosylamine-substituted peptides in heated aqueous systems

2015

View full text Add to dashboard Cite

show abstract

“…The accuracy of the measured values with the theoretical values was checked according to the procedure described by Staempfli and coworkers (30). On the basis of knowing the amount of 1 and d-1 in the mixture, the theoretical enrichment of d-1 was calculated for each calibration point and expressed in mol percent excess (MPE).…”

Section: Carbonmentioning

confidence: 99%

Synthesis of trans‐4,5‐epoxy‐(E)‐2‐decenal and its deuterated analog used for the development of a sensitive and selective quantification method based on isotope dilution assay with negative chemical ionization

Lin

Fay

Welti

et al. 1999

Lipids

Self Cite

View full text Add to dashboard Cite

The volatile compound trans-4,5-epoxy-(E)-2-decenal (1) was synthesized in two steps with good overall yields. The newly developed method is based on trans-epoxidation of (E)-2-octenal with alkaline hydrogen peroxide followed by a Wittig-type chain elongation with the ylide formylmethylene triphenylphosphorane. For the synthesis of [4,5-2H2]-trans-4,5-epoxy-(E)-2-decenal (d-1), [2,3-2H2]-(E)-2-octenal was prepared by reduction of 2-octyn-1-ol with lithium aluminum deuteride and subsequent oxidation of [2,3-2H2]-(E)-2-octen-1-ol with manganese oxide. Compound d1 was used as internal standard for the quantification of 1 by isotope dilution assay. Among various mass spectrometry (MS) ionization techniques tested, negative chemical ionization with ammonia as reagent gas gave best results with respect to both sensitivity and selectivity. The detection limit was found to be at about 1 pg of the analyte introduced into the gas chromatography-MS system.

show abstract

“…3A), particularly when the amount ratios were extended to values higher than 10. This is due to the natural 13 C abundance in the analyte, which coincided with the acquired ions of the deuterated IS, i.e., interference of natural isotope enrichment at higher mass or of the isotopic impurity at lower mass (26). To facilitate work within a linear range, we used only the lower part of the calibration curve, which showed excellent linearity (Fig.…”

Section: Resultsmentioning

confidence: 99%

“…The accuracy of the measured values compared to the theoretical values was checked according to the procedure recently described (26). Knowing the amount of analyte and labeled IS in the mixture, the theoretical enrichment of d-IS was calculated for each calibration point (data not shown) and expressed in mol% excess.…”

Section: Resultsmentioning

confidence: 99%

Quantification of key odorants formed by autoxidation of arachidonic acid using isotope dilution assay

Lin

Fay

Welti

et al. 2001

Lipids

Self Cite

View full text Add to dashboard Cite

Six odor-active compounds generated by autoxidation of arachidonic acid (AA) were quantified by isotope dilution assay (IDA), i.e., hexanal (1), 1-octen-3-one (2), (E,Z)-2,4-decadienal (3), (E,E)-2,4-decadienal (4), trans-4,5-epoxy-(E)-2-decenal (5), and (E,Z,Z)-2,4,7-tridecatrienal (6). Compound 1 was the most abundant odorant with about 700 mg/100 g autoxidized AA, which corresponds to 2.2 mol% yield. Based on the odor activity values (ratio of concentration to odor threshold), odorants 3 (fatty) and 5 (metallic) showed the highest sensory contribution followed by 1 (green), 2 (mushroom-like), 6 (egg white-like), and 4 (fatty). For the first time, reliable quantitative results are reported for odorants 1-6 in autoxidized AA, in particular odorant 6, which is a characteristic compound found in autoxidized AA. Synthesis of deuterated 6, required for IDA, is described in detail. The formation of odorants 1-6 by autoxidation of AA is discussed with respect to the quantitative data.

show abstract

Study on the decomposition of the amadori compoundN-(1-deoxy-D-fructos-1-y1)-glycine in model systems: Quantification by fast atom bombardment tandem mass spectrometry

Cited by 34 publications

References 14 publications

Oxidative degradation of N ε-fructosylamine-substituted peptides in heated aqueous systems

Oxidative degradation of N ε-fructosylamine-substituted peptides in heated aqueous systems

Synthesis of trans‐4,5‐epoxy‐(E)‐2‐decenal and its deuterated analog used for the development of a sensitive and selective quantification method based on isotope dilution assay with negative chemical ionization

Quantification of key odorants formed by autoxidation of arachidonic acid using isotope dilution assay

Contact Info

Product

Resources

About