On the reaction of glyoxal with proteins |
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Authors: | U Schwarzenbolz T Henle Rainer Haeßner Henning Klostermeyer |
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Affiliation: | Lehrstuhl für Milchwissenschaft, Technische Universit?t München, V?ttinger Strasse 45, D-85350 Freising-Weihenstephan, Germany, DE Lehrstuhl II für Organische Chemie, Technische Universit?t München, Lichtenbergstrasse 4, D-85748 Garching, Germany, DE
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Abstract: | The reaction of arginine and arginine derivatives with glyoxal under mild conditions revealed the formation of a previously
unknown amino acid, designated as “Glarg”. 1H-, 15N- and 13C-NMR analysis of the new compound elucidated its structure to be 1-(4-amino-4-carboxybutyl)-2-imino-5-oxo-imidazolidine.
Experiments with solutions containing N
α
-acetylarginine and glyoxal showed that “Glarg” is formed quickly under physiological conditions, but is labile at higher
temperatures as well as at low pH values. After incubation of β-casein with glyoxal, the formation of protein-bound “Glarg”
in enzymatic hydrolysates via amino acid analysis could be demonstrated. Due to the fast reaction of glyoxal with arginine
residues, under physiological conditions, proteins may act as scavengers for glyoxal.
Received: 8 November 1996 / Revised version: 10 January 1997 |
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Keywords: | Arginine Glyoxal Maillard reaction Protein modification 1-(4-Amino-4-carboxybutyl)-2-imino-5-oxo-imidazolidine |
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