Fate of the amino acid in glucose-glycine melanoidins investigated by solid-state nuclear magnetic resonance (NMR)

Journal of Agricultural and Food Chemistry
Xiaowen Fang, Klaus Schmidt-Rohr

Abstract

The fate of the amino acid in the model Maillard reaction between glucose and glycine in a 1:1 molar ratio has been investigated by applying advanced 13C and 15N solid-state nuclear magnetic resonance (NMR) techniques to 13C- and 15N-labeled melanoidins formed in dry and solution reactions. Quantitative 13C NMR shows that approximately 23% of carbon is from glycine; the approximately 2% loss compared to the 25% glycine C in the reactants is due to the COO moiety being liberated as CO2 (Strecker degradation). 13C J-modulation experiments on melanoidins made from doubly 13C-labeled glycine show that the C-C backbone bond of about two-thirds of the incorporated amino acid stays intact, and about half of all glycine is incorporated as N-CH2-COO without fragmentation. Degradation processes without CO2 loss affect about one-eighth of glycine in dry reaction and about one-fourth in solution. These results indicate that Strecker degradation affects about one-fourth (dry reaction) to one-third (in solution) of all glycine but is not the main pathway of glycine incorporation. Spectra of Strecker degradation products show that C2 of glycine reacts to form N-CH3, C-CHn-C, or aromatic units, but not pyrazines or pyridines. The gycine-C1 car...Continue Reading

References

Jul 23, 1999·Archives of Biochemistry and Biophysics·P Chellan, R H Nagaraj
Jun 27, 2002·Journal of Agricultural and Food Chemistry·Kourosch Abbaspour TehraniNorbert De Kimpe
Jul 10, 2003·Journal of Agricultural and Food Chemistry·An AdamsNorbert De Kimpe
Jun 9, 2005·Journal of Magnetic Resonance·J-D Mao, K Schmidt-Rohr

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Citations

Aug 31, 2012·Journal of Peptide Science : an Official Publication of the European Peptide Society·Ping LiuJohn Nsor-Atindana
Jun 28, 2017·International Journal of Biological Macromolecules·Farhad GaravandReza Mohammadi
Jan 30, 2015·Magnetic Resonance in Chemistry : MRC·Caroline M Preston
Mar 11, 2019·Journal of Magnetic Resonance·Pu Duan, Klaus Schmidt-Rohr
May 30, 2017·Progress in Nuclear Magnetic Resonance Spectroscopy·Jingdong MaoKlaus Schmidt-Rohr
Nov 5, 2011·Langmuir : the ACS Journal of Surfaces and Colloids·Camillo FalcoNiki Baccile
Dec 30, 2010·Journal of Agricultural and Food Chemistry·Xiaowen Fang, Klaus Schmidt-Rohr

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