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Information on EC - fructosyl amine oxidase (glucosone-forming)

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IUBMB Comments
Reducing sugars such as glucose react with amino groups in proteins via the spontaeous Maillard reaction, forming an unstable product that undergoes spontaneous rearrangement to a keto amine compound. These reactions are known as glycation reactions, and the stable products are known as Amadori products. This enzyme, which contains an FAD cofactor, catalyses a deglycation reaction that regenerates the amine reactant. By-products are glucosone and hydrogen peroxide. The enzymes have been reported from fungi and bacteria, but not from higher eukaryotes. Specific enzymes differ in their substrate specificity. cf. EC, fructosyl amine oxidase (fructosamine-forming).
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The enzyme appears in viruses and cellular organisms
Reaction Schemes
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an N-(1-deoxy-D-fructos-1-yl)amine
amadoriase i, fructosyl amino acid oxidase, amadoriase ii, amadoriase, agae-like protein, faod-ao2, faoao2, faox-ii, faod-ao1, faoao1, more
a 2-[(3S,4R,5R)-3,4,5,6-tetrahydroxy-2-oxohexylidene]amine + H2O = D-glucosone + an amine
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(1b), spontaneous
an N-(1-deoxy-D-fructos-1-yl)amine + O2 + H2O = D-glucosone + an amine + H2O2
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overall reaction
an N-(1-deoxy-D-fructos-1-yl)amine + O2 = a 2-[(3S,4R,5R)-3,4,5,6-tetrahydroxy-2-oxohexylidene]amine + H2O2
show the reaction diagram