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Mechanism of Protein Modification by Glyoxal and Glycolaldehyde, Reactive Intermediates of the Maillard Reaction

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Glomb, Marcus A., Monnier, Vincent M.·1995·Journal of Biological Chemistry

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Abstract

The role of glyoxal and glycolaldehyde in protein cross-linking and N epsilon-(carboxymethyl)lysine (CML) formation during Maillard reaction under physiological conditions was investigated. Incubation of bovine serum albumin with these reagents lead to rapid formation of C-2-imine cross-links and CML. Initial CML formation rate from glyoxal was not dependent on oxidation, suggesting an intramolecular Cannizzaro reaction. CML formation from glucose/lysine or Amadori product of both was strongly dependent on oxidation. Blocking of Amadori product by boric acid totally suppressed CML formation from Amadori product, but only by 37% in the glucose/lysine system. Trapping of glyoxal with aminoguanidine hardly suppressed CML formation from Amadori product, whereas it blocked 50% of CML production in the glucose/lysine system. While these results would support a significant role for glucose autoxidation in CML formation, the addition of lysine to a glucose/aminoguanidine incubation system catalyzed glyoxal-triazine formation 7-fold, thereby strongly suggesting that glucose autoxidation is not a factor for glyoxal-mediated CML formation. Based on these results, it can be estimated that approximately 50% of the CML forming in a glucose/lysine system originates from oxidation of Amadori product, and 40-50% originates from a pre-Amadori stage largely independent from glucose autoxidation. This step may be related to the so-called Namiki pathway of the Maillard reaction.

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Authors: Glomb, M. A., & Monnier, V. M.
Affiliations: Case Western Reserve University (US)
Corresponding author: Glomb, Marcus A.
ORCID: Glomb, Marcus A.
Monnier, Vincent M.
Venue: Journal of Biological Chemistry
Publisher: Elsevier BV
Published: 1995-04
Volume: 270
Issue: 17
Pages: 10017-10026
ISSN: 0021-9258 (ISSN-L)
DOI: 10.1074/jbc.270.17.10017
OpenAlex: W2017214714
Cited by: 576
References: 28
Citations by year: 2026: 10 · 2025: 9 · 2024: 13 · 2023: 13 · 2022: 12 · 2021: 24 · 2020: 8 · 2019: 12 · 2018: 24 · 2017: 16 · 2016: 19 · 2015: 20 · 2014: 22 · 2013: 19 · 2012: 18
FWCI: 11.39
Type: journal article
Language: en
Open access: hybrid
doi.org
Licence: cc-by
www.elsevier.com/tdm/userlicense/1.0/ (tdm)
creativecommons.org/licenses/by/4.0/ (vor, 9357 d)
Locations: Journal of Biological Chemistry (publishedVersion, cc-by)
PubMed (publishedVersion)
Funders: National Institutes of Health (5r01ag005601-13)
National Institute on Aging (AG 05601)
National Eye Institute (EY 07099, R01EY007099)
Topics: Life Sciences › Biochemistry, Genetics and Molecular Biology › Clinical Biochemistry › Advanced Glycation End Products research
Life Sciences › Agricultural and Biological Sciences › Food Science › Potato Plant Research
Life Sciences › Biochemistry, Genetics and Molecular Biology › Molecular Biology › Glycosylation and Glycoproteins Research
Keywords: Maillard reaction, glyoxal, glycolaldehyde, carboxymethyllysine, protein cross-linking, bovine serum albumin, Amadori products, Cannizzaro reaction, protein oxidation, boric acid, aminoguanidine
MeSH terms: Acetaldehyde, Chromatography, High Pressure Liquid, Chromatography, Thin Layer, Electrophoresis, Polyacrylamide Gel, Glyoxal, Lysine, Gas Chromatography-Mass Spectrometry, Oxidation-Reduction, Proteins, Maillard Reaction

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Mechanism of Protein Modification by Glyoxal and Glycolaldehyde, Reactive Intermediates of the Maillard Reaction

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