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Pyridoxamine (PM) could competitively protect amino groups in proteins from glycating agents. Although PM is expected to react with saccharides, available data therein are limited. In this study, a novel hydrophilic compound from a model reaction solution containing PM and xylose was isolated and identified as (6a R ,9a R )-1,8,9-trihydroxy-2,6a-dimethyl-6a,9a-dihydrocyclopenta[5,6]pyrano[3,4- c ]pyridin-7(5 H )-one with a tricyclic structure. This compound appeared to be specifically formed from pentose via 1-deoxypentosone, and its formation was facilitated over a pH range of 7.0–8.0. After heating at 90 °C for 5 h in a reaction mixture containing 30 mM PM and pentose at pH 7.4, this compound was obtained at a yield of 6.95–8.53 mM.

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Isolation, identification, and proposed formation mechanism of a novel hydrophilic compound formed by Maillard reaction between pyridoxamine and pentose