Carboxymethyllysine, formation

Al-Abed Y and Bucala R (1995) N-carboxymethyllysine formation by direct addition of glyoxal to lysine during the Maillard reaction. Bioorg Med Chem Lett 5, 2161-2162. 

Hartkopf, J. and Erbersdobler, H.F. (1995). Model experiments with sausage meat on the formation of 7V -carboxymethyllysine, Z. Lebensm. Unters. Forsch., 201, 27-29. 

The increase of carboxymethyllysine (batch 1) and pentosidine (batches 1 and 11) thus observed provided additional proof for fhe Maillard reaction in caries (fable 3, figs. 2, 3). The pentosidine level ranged from abouf equal fo a manifold of the level in sound dentin. The formation of pentosidine can only account for a fraction of the increase in 328/378 fluorescence, which is in accordance with a major contribution from a different fluorophore as stated above. Unfortunately, an increase of dify-rosine as expected from fhe gain in 317/407 fluorescence (fable 2) could not be substantiated unequivocally by HPLC analysis because dityrosine co-eluted with lysylpyridinoline. Even if we would consider dityrosine to originate the lysylpyridinoline peaks observed in HPLC of carious dentin, but not of sound dentin, only one quarter of the increase in 317/407 fluorescence would derive from difyrosine. 

R. Badoud, L. Fay, F. Hunston, and G. Pratz, Periodate oxidative degradation of Amadori compounds. Formation of V -carboxymethyllysine and... 

As an alternative method for the above mentioned food items we proved the formation of N -carboxymethyllysine (CML) in a model system of several sugars and lysine (24) or casein, respectively. CML, an oxidative decomposition product of e-fructoselysine was identified for the first time in 1985 (25) in biological material and later also in food items (26, 27). This new compound can be detected... 

Figure 5. Formation of N -Carboxymethyllysine (CML) in a model system with lysine monohydrochloride and various reducing sugars after heating at 98°C (recalculated from Ruttkat and Erbersdobler, 1995).

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