Glycine-Xylose Amadori Compound Formation Tracing through Maillard Browning Inhibition by 2-Threityl-thiazolidine-4-carboxylic Acid Formation from Deoxyosone and Exogenous Cysteine

The browning inhibition of cysteine on the Maillard reaction of glycine-xylose performed under stepwise increased temperature was investigated. The browning degrees of the final products prepared with cysteine addition at different time points were found dissimilar, and the addition time point of cysteine yielding the lightest browning products was consistent with the time when the glycine-xylose Amadori rearrangement product (GX-ARP) reached its maximum yield. To clarify the reason for browning inhibition caused by cysteine, the evolution of key browning precursors formed in the GX-ARP model with cysteine involved was investigated by HPLC with a diode array detector. The results on the browning degree of the thermal reaction products of GX-ARP with cysteine addition showed great inhibition of α-dicarbonyl generation, which resulted in a significant increase in the activation energy of GX-ARP conversion to browning formation during heat treatment. Strong evidence suggested that the additional cysteine got involved in GX-ARP degradation and reacted with the deoxyosones derived from GX-ARP to yield cyclic 2-threityl-thiazolidine-4-carboxylic acid (TTCA). TTCA formation shunted the degradation of deoxyosones into short-chain α-dicarbonyls, which were important browning precursors, and consequently inhibited the Maillard browning.