Journal of Agricultural and Food Chemistry 2008-04-09

Formation of peptide-bound Heyns compounds.

René Krause, Kathrin Schlegel, Evelyn Schwarzer, Thomas Henle

Index: J. Agric. Food Chem. 56(7) , 2522-7, (2008)

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Abstract

The reaction of the Nalpha-hippuryllysine (BzGK) with fructose was investigated in two model systems to obtain an insight in fructose-induced modification of lysine in bakery products. After BzGK and fructose had been heated in a buffered low-moisture model system (80 degrees C, 60 min, aW = 0.86, pH 7.4), formation of epimeric Heyns compounds Nalpha-hippuryl-Nepsilon-glucosyl-lysine (BzGGlcK) and Nalpha-hippuryl-Nepsilon-mannosyl-lysine (BzGManK) was clearly demonstrated using RP-HPLC with UV as well as MS detection. The Amadori compound Nalpha-hippuryl-Nepsilon-fructosyl-lysine (BzGFruK) was formed in glucose-containing samples. When BzGK was added to the dough of fructose-containing biscuits, the Heyns compounds were detectable after baking at 175 degrees C for 7 min. The yields of the Heyns compounds in the fructose-containing biscuits and the yield of the Amadori compound in the glucose-containing biscuits were determined to 33 and 63%, pointing to the fact that formation of substantial amounts of Heyns products is very likely in fructose-containing bakery products.