Analysis of the 220-MHz, P.M.R. spectra of some products of the amadori and heyns rearrangements

Altena, Johannes H.; Ouweland, G. A. M. van den; Teunis, C.J.; Tjan, S.B.

doi:10.1016/s0008-6215(00)85980-7

Cited by 33 publications

(7 citation statements)

References 20 publications

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“…In addition, 13 C NMR spectroscopy (Figure c) shows another three carbon resonance signals which were not shown in HSQC, indicating they were quaternary carbon and carbons connected with carboxylate groups of the glutamate backbone. Moreover, these spectra of the ARP were recorded for solution in D 2 O and in good agreement with relative research studies, showing that the primary component exists in the β-cyclic pyranose form. − Although there is a tautomeric equilibrium of N -(β- d -deoxyfructos-1-yl)- l -glutamic acid in D 2 O, its β-fructopyranose form is more stable and usually constitutes over 80% of the whole conformation when the environment temperature is under about 30 °C. , Despite its α and β-furanose forms, rarely, the α-pyranose form was detected in the food system . Overall, these data suggested that N -(β- d -deoxyfructos-1-yl)- l -glutamic acid was the primary form of prepared ARP.…”

Section: Resultssupporting

confidence: 75%

Maillard Mimetic Food-Grade Synthesis of N-(β-d-Deoxyfructos-1-yl)-l-glutamic Acid and N-(β-d-Deoxyfructos-1-yl)-β-alanyl-l-histidine by a Combination of Lyophilization and Thermal Treatment

Zhang

Zhao

Gao

et al. 2020

J. Agric. Food Chem.

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A typical glycoconjugate of glutamic acid, namely, N-(β-D-deoxyfructos-1-yl)-L-glutamic acid, was successfully synthesized as the primary isomer in a yield of 96.08% using a food-grade preparation method, and its chemical structure was clearly demonstrated by mass spectrometry and 1D/2D NMR. The reaction kinetics of glucose and glutamic acid were systematically studied to investigate the effect of lyophilization and thermal treatment on the conversion of reactants to their corresponding Amadori rearrangement product (ARP). Interestingly, besides the initial pH value, temperature, and heating time, the initial concentration of glutamic acid also influenced the final yield because intramolecular dehydration occurred at the same time, competing with the Maillard reaction and degrading reaction. Moreover, a similar Amadori compound of carnosine was also prepared in a yield of about 66.38% and the yield could be further improved to 95% after condition optimization. One major isomer of the corresponding ARP of the peptide was confirmed to be N-(β-D-deoxyfructos-1-yl)-β-alanyl-L-histidine by structure characterization, indicating that this is a good method to prepare the N-(β-D-deoxyfructos-1-yl)-amino acid/peptide.

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Section: Resultssupporting

confidence: 75%

Maillard Mimetic Food-Grade Synthesis of N-(β-d-Deoxyfructos-1-yl)-l-glutamic Acid and N-(β-d-Deoxyfructos-1-yl)-β-alanyl-l-histidine by a Combination of Lyophilization and Thermal Treatment

Zhang

Zhao

Gao

et al. 2020

J. Agric. Food Chem.

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“…4D). These 2 characteristic features of the 'H-NMR spectra of Amadori conjugates have been verified previously by other workers (16). The 'H-NMR spectrum of the Amadori product formed by heating glucuronic acid and lysine (purified by gel filtration on Sephadex G-25 in H 2 O) was comparable to that of the fragment isolated from ATH [single resonance at 3.2 ppm and no anomeric proton signals (Fig.…”

Section: Resultssupporting

confidence: 84%

Polypeptide-Polysaccharide Conjugates Produced by Spontaneous Non-Enzymatic Glycation

Berry¹,

Chan²,

Andrew³

1998

Journal of Biochemistry

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A fundamental dogma has developed over the past 20 years that non-enzymatic glycation involving saccharide chains of greater than 3 to 4 residues is an extremely unlikely reaction. Our investigations using glycosaminoglycans have shown that, given sufficient time, polypeptide-polysaccharide conjugates form via the Schiff base-Amadori rearrangement mechanism. Further, even though these straight chain polysaccharides are relatively charged and sterically hindered, spontaneous glycation can also occur in vivo. A complete reinvestigation of all aldose terminating polysaccharides is required to elucidate this new class of macromolecules, which is likely to contain unusual polypeptide-polysaccharide combinations and functions.

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“…We have made assignments for F-Asp and F-Asn only for the predominant form which we assume to be the β-pyranose. Partial assignments for the proton and carbon spectra have been made previously 15,16 . In agreement with Altena et al 15 , the C1′ position exhibits clear deuterium isotope shifts consistent with partial exchange with the D 2 O solvent.…”

Section: Methodsmentioning

confidence: 99%

Synthesis of 6-phosphofructose aspartic acid and some related Amadori compounds

Hansen

Behrman

2016

Carbohydrate Research

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Analysis of the 220-MHz, P.M.R. spectra of some products of the amadori and heyns rearrangements

Cited by 33 publications

References 20 publications

Maillard Mimetic Food-Grade Synthesis of N-(β-d-Deoxyfructos-1-yl)-l-glutamic Acid and N-(β-d-Deoxyfructos-1-yl)-β-alanyl-l-histidine by a Combination of Lyophilization and Thermal Treatment

Maillard Mimetic Food-Grade Synthesis of N-(β-d-Deoxyfructos-1-yl)-l-glutamic Acid and N-(β-d-Deoxyfructos-1-yl)-β-alanyl-l-histidine by a Combination of Lyophilization and Thermal Treatment

Polypeptide-Polysaccharide Conjugates Produced by Spontaneous Non-Enzymatic Glycation

Synthesis of 6-phosphofructose aspartic acid and some related Amadori compounds

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