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Information on EC 1.5.3.25 - fructosyl amine oxidase (glucosone-forming)
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1.5.3.25 fructosyl amine oxidase (glucosone-forming)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 1.5.3.26, fructosyl amine oxidase (fructosamine-forming).
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The expected taxonomic range for this enzyme is: Bacteria, Eukaryota
Reaction Schemes
an N-(1-deoxy-D-fructos-1-yl)amine
+
+
=
+
+
Synonyms
amadoriase i, fructosyl amino acid oxidase, amadoriase ii, amadoriase, agae-like protein, faod-ao2, faoao2, faox-ii, faod-ao1, faoao1, 
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SYNONYM 
ORGANISM
UNIPROT
COMMENTARY 
LITERATURE
amadoriase
FAOX-C
amadoriase
-
-
-
-
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REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
a 2-[(3S,4R,5R)-3,4,5,6-tetrahydroxy-2-oxohexylidene]amine + H2O = D-glucosone + an amine
(1b), spontaneous
-
-
-
an N-(1-deoxy-D-fructos-1-yl)amine + O2 + H2O = D-glucosone + an amine + H2O2
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
(1a)
-
-
-
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SYSTEMATIC NAME
IUBMB Comments
N-(1-deoxy-D-fructos-1-yl)amine:oxygen 2-oxidoreductase (glucosone-forming)
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 1.5.3.26, fructosyl amine oxidase (fructosamine-forming).
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SUBSTRATE
PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate)
(Substrate)
LITERATURE
(Substrate)
(Substrate)
COMMENTARY
(Product)
(Product)
LITERATURE
(Product)
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
D-difructosyllysin + O2 + H2O
glucosone + lysine + H2O2
-
-
-
?
fructosyl-L-lysine + O2 + H2O
glucosone + L-lysine + H2O2
-
-
-
?
glucose 6-phosphate + alpha-Boc-L-lysine + ?
fructosyl-6-phosphate alpha-Boc-L-lysine + ?
-
-
-
r
glucose 6-phosphate + glycine + ?
fructosyl-6-phosphate glycine + ?
-
-
-
r
glucose 6-phosphate + L-histidine + ?
fructosyl-6-phosphate L-histidine + ?
-
-
-
r
glucose 6-phosphate + L-lysine + ?
fructosyl-6-phosphate L-lysine + ?
-
-
-
r
glucose 6-phosphate + poly-L-lysine + ?
fructosyl-6-phosphate poly-L-lysine + ?
-
-
-
r
Nalpha-fructosyl L-lysine + O2 + H2O
glucosone + L-lysine + H2O2
-
-
-
?
Nalpha-fructosyl-Nepsilon-acetyl-L-lysine + O2 + H2O
glucosone + Nepsilon-acetyl-L-lysine + H2O2
-
substrate of isoform amadoriase II
-
-
?
Nepsilon-(1-deoxy-D-fructos-1-yl)-L-lysine + O2 + H2O
? + L-lysine + H2O2
-
-
-
-
?
Nepsilon-fructosyl L-Lys-L-Leu + O2 + H2O
glucosone + L-Lys-L-Leu + H2O2
-
-
-
-
?
Nepsilon-fructosyl L-Lys-L-Phe + O2 + H2O
glucosone + L-Lys-L-Phe + H2O2
-
-
-
-
?
Nepsilon-fructosyl Nalpha-acetyl-L-Lys-D-Ala-L-Ala + O2 + H2O
glucosone + Nalpha-acetyl-L-Lys-D-Ala-L-Ala + H2O2
-
-
-
-
?
Nepsilon-fructosyl Nalpha-acetyl-L-Lys-D-D-Lys-Sar-Glu + O2 + H2O
glucosone + Nalpha-acetyl-L-Lys-D-Lys-Sar-Glu + H2O2
-
-
-
-
?
Nepsilon-fructosyl Nalpha-acetyl-L-lysine-N-methylamide + O2 + H2O
glucosone + acetyl-L-lysine-N-methylamide + H2O2
-
-
-
-
?
Nepsilon-fructosyl poly-L-lysine + O2 + H2O
glucosone + poly-L-lysine + H2O2
poor substrate
-
-
?
Nepsilon-fructosyl-Nalpha-benzyloxycarbonyl-L-lysine + O2 + H2O
glucosone + N-alpha-benzyloxycarbonyl-L-lysine + H2O2
Nepsilon-fructosyl-Nalpha-benzyloxycarbonyl-L-lysine + O2 + H2O
glucosone + N-alpha-benzyloxycarbonyl-L-valine + H2O2
-
-
-
-
?
Nepsilon-fructosyl-Nalpha-benzyloxycarbonyl-L-valine + O2 + H2O
glucosone + N-alpha-benzyloxycarbonyl-L-valine + H2O2
-
-
-
-
?
Nepsilon-fructosyl-Nalpha-t-butoxycarbonyl-L-lysine + O2 + H2O
glucosone + Nalpha-t-butoxycarbonyl-L-lysine + H2O2
-
-
-
-
?
S: Nepsilon-fructosyl Nalpha-benzyloxycarbonyl-L-lysine + O2 + H2O
glucosone + Nalpha-benzyloxycarbonyl-L-lysine + H2O2
-
-
-
?
epsilon-fructosyl-aminocaproate + O2 + H2O
glucosone + aminocaproate + H2O2
-
-
-
-
?
epsilon-fructosyl-aminocaproate + O2 + H2O
glucosone + aminocaproate + H2O2
Fusarium oxysporum f. sp. raphani NBRC 9972
-
-
-
-
?
fructosyl adamantanamine + O2 + H2O
glucosone + adamantanamine + H2O2
-
-
-
?
fructosyl adamantanamine + O2 + H2O
glucosone + adamantanamine + H2O2
poor substrate of isoform amadoriases I
-
-
?
fructosyl adamantanamine + O2 + H2O
glucosone + adamantanamine + H2O2
-
poor substrate of isoform amadoriases I
-
-
?
fructosyl glycine + O2 + H2O
glucosone + glycine + H2O2
-
-
-
?
fructosyl glycine + O2 + H2O
glucosone + glycine + H2O2
-
-
-
?
fructosyl glycine + O2 + H2O
glucosone + glycine + H2O2
-
-
-
?
fructosyl glycine + O2 + H2O
glucosone + glycine + H2O2
poor substrate of isoform amadoriases I
-
-
?
fructosyl L-alanine + O2 + H2O
glucosone + L-alanine + H2O2
-
-
-
-
?
fructosyl L-alanine + O2 + H2O
glucosone + L-alanine + H2O2
Fusarium oxysporum f. sp. raphani NBRC 9972
-
-
-
-
?
fructosyl L-lysine + O2 + H2O
glucosone + L-lysine + H2O2
-
-
-
?
fructosyl L-phenylalanine + O2 + H2O
glucosone + L-phenylalanine + H2O2
-
-
-
?
fructosyl L-phenylalanine + O2 + H2O
glucosone + L-phenylalanine + H2O2
-
-
-
?
fructosyl L-valine + O2 + H2O
glucosone + L-valine + H2O2
-
-
-
?
fructosyl L-valine + O2 + H2O
glucosone + L-valine + H2O2
-
-
-
?
fructosyl L-valine + O2 + H2O
glucosone + L-valine + H2O2
-
-
-
?
fructosyl L-valine + O2 + H2O
glucosone + L-valine + H2O2
-
-
-
?
fructosyl L-valine + O2 + H2O
glucosone + L-valine + H2O2
-
-
-
-
?
fructosyl L-valine + O2 + H2O
glucosone + L-valine + H2O2
Fusarium oxysporum f. sp. raphani NBRC 9972
-
-
-
-
?
fructosyl L-valine + O2 + H2O
glucosone + L-valine + H2O2
-
-
-
?
fructosyl L-valine + O2 + H2O
glucosone + L-valine + H2O2
poor substrate of isoform amadoriases I
-
-
?
fructosyl poly-L-lysine + O2 + H2O
glucosone + poly-L-lysine + H2O2
-
-
-
?
fructosyl poly-L-lysine + O2 + H2O
glucosone + poly-L-lysine + H2O2
-
-
-
-
?
fructosyl propylamine + O2 + H2O
glucosone + propylamine + H2O2
-
-
-
?
fructosyl propylamine + O2 + H2O
glucosone + propylamine + H2O2
-
-
-
-
?
gamma-fructosyl-aminobutanoate + O2 + H2O
glucosone + aminobutanoate + H2O2
-
-
-
-
?
gamma-fructosyl-aminobutanoate + O2 + H2O
glucosone + aminobutanoate + H2O2
Fusarium oxysporum f. sp. raphani NBRC 9972
-
-
-
-
?
Nepsilon-fructosyl L-lysine + O2 + H2O
glucosone + L-lysine + H2O2
-
-
-
?
Nepsilon-fructosyl L-lysine + O2 + H2O
glucosone + L-lysine + H2O2
-
-
-
?
Nepsilon-fructosyl-L-lysine + O2 + H2O
glucosone + L-lysine + H2O2
-
-
-
?
Nepsilon-fructosyl-L-lysine + O2 + H2O
glucosone + L-lysine + H2O2
poor substrate of isoform amadoriases I
-
-
?
Nepsilon-fructosyl-Nalpha-benzyloxycarbonyl-L-lysine + O2 + H2O
glucosone + N-alpha-benzyloxycarbonyl-L-lysine + H2O2
-
-
-
-
?
Nepsilon-fructosyl-Nalpha-benzyloxycarbonyl-L-lysine + O2 + H2O
glucosone + N-alpha-benzyloxycarbonyl-L-lysine + H2O2
Fusarium oxysporum f. sp. raphani NBRC 9972
-
-
-
-
?
additional information
?
-
no substrates: glycated protein or Nepsilon-fructosyl-L-lysine, Nepsilon-fructosyl-Nalpha-(benzyloxycarbonyl)-L-lysine
-
-
-
additional information
?
-
-
no substrates: glycated protein or Nepsilon-fructosyl-L-lysine, Nepsilon-fructosyl-Nalpha-(benzyloxycarbonyl)-L-lysine
-
-
-
additional information
?
-
fructosyl-alpha-L-amino acids are the substrate having the highest susceptibility to the enzyme, but N-fructosyl derivatives of other materials, such as p-amino acids, L-imino acids, D-amino acids, alkyl amines, and ammonia, show almost no susceptibility
-
-
-
additional information
?
-
no substrate: Nepsilon-D-fructosyl-Nalpha-formyl-L-lysine
-
-
-
additional information
?
-
-
Kmvalue decreases with the length of peptide substrate, being slightly reduced for dipeptides, and is around 10 mM for tri- and tetrapeptides. Glycated proteins are not substrates of the enzyme, but when amadoriase I is added during the glycation reaction, a significant reduction of Amadori product formation is observed on both peptides and proteins
-
-
-
additional information
?
-
no substrates: fructosyl L-valine, L-Pipecolate, sarcosine, and L-proline
-
-
-
additional information
?
-
no substrates: fructosyl L-valine, L-Pipecolate, sarcosine, and L-proline
-
-
-
additional information
?
-
-
no substrates: fructosyl L-valine, L-Pipecolate, sarcosine, and L-proline
-
-
-
additional information
?
-
no substrates: L-Pipecolate, sarcosine, and L-proline
-
-
-
additional information
?
-
no substrates: L-Pipecolate, sarcosine, and L-proline
-
-
-
additional information
?
-
-
no substrates: L-Pipecolate, sarcosine, and L-proline
-
-
-
additional information
?
-
FrlB amadoriase is capable of catalyzing in the reverse reaction the formation of Amadori products on a number of free amino acids and on polypeptides as well
-
-
-
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COFACTOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
FAD
-
both isoforms contain the FAD cofactor-binding consensus sequence Gly-X-Gly-X-X-Gly within the N-terminal sequence
FAD
-
enzyme contains 1 mol of FAD per mol. FAD is covalently linked to Cys342
FAD
FAD is covalnetly attached. Sequence contains the FAD-binding consensus sequence GXGXXG
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METALS and IONS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
4-hydroxyphenylglyoxal
-
inhibition of amadoriase II enzyme activity toward fructosyl glycine, with less effect on the enzymatic activity toward fructosyl propylamine
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KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
6.55
epsilon-fructosyl-aminocaproate
-
wild-type, pH 8.0, temperature not specified in the publication
-
27.8
epsilon-fructosyl-aminocaproate
-
mutant K373W, pH 8.0, temperature not specified in the publication
-
0.18
fructosyl glycine
mutant R114S, 30°C, pH not specified in the publication
-
0.2
fructosyl glycine
mutant E71S, 30°C, pH not specified in the publication
-
0.21
fructosyl glycine
mutant E71R, 30°C, pH not specified in the publication
-
0.24
fructosyl glycine
wild-type, 30°C, pH not specified in the publication
-
0.58
fructosyl glycine
mutant T60A/A188G/M244L/N257S/L261M, pH 8, 37°C
-
0.86
fructosyl glycine
mutant Y60F, 30°C, pH not specified in the publication
-
1.25
fructosyl glycine
mutant K368M, 30°C, pH not specified in the publication
-
2.06
fructosyl glycine
mutant E71R/R114E, 30°C, pH not specified in the publication
-
2.45
fructosyl glycine
mutant R112E, 30°C, pH not specified in the publication
-
2.5
fructosyl glycine
mutant R114E, 30°C, pH not specified in the publication
-
0.98
fructosyl L-alanine
-
wild-type, pH 8.0, temperature not specified in the publication
-
29.4
fructosyl L-alanine
-
mutant K373W, pH 8.0, temperature not specified in the publication
-
0.76
fructosyl L-valine
-
mutant R94W, pH 8.0, temperature not specified in the publication
-
0.88
fructosyl L-valine
-
wild-type, presence of 20 mM MgCl2, pH 8.0, temperature not specified in the publication
-
1.01
fructosyl L-valine
-
wild-type, pH 7.5, temperature not specified in the publication
-
1.32
fructosyl L-valine
-
mutant R94F, pH 8.0, temperature not specified in the publication
-
1.37
fructosyl L-valine
-
wild-type, pH 8.0, temperature not specified in the publication
-
1.38
fructosyl L-valine
pH 8.5, temperature not specified in the publication
-
1.5
fructosyl L-valine
mutant T60A/A188G/M244L/N257S/L261M, pH 8, 37°C
-
2.33
fructosyl L-valine
-
mutant R94L, pH 8.0, temperature not specified in the publication
-
14.3
fructosyl L-valine
-
mutant K373W, presence of 20 mM MgCl2, pH 8.0, temperature not specified in the publication
-
17.6
fructosyl L-valine
-
mutant K373V, pH 8.0, temperature not specified in the publication
-
18.4
fructosyl L-valine
-
mutant K373T, pH 8.0, temperature not specified in the publication
-
19
fructosyl L-valine
-
mutant K373M, pH 8.0, temperature not specified in the publication
-
20.8
fructosyl L-valine
-
mutant K373W, pH 8.0, temperature not specified in the publication
-
29.9
fructosyl L-valine
-
mutant K373R, pH 8.0, temperature not specified in the publication
-
9.63
gamma-fructosyl-aminobutanoate
-
wild-type, pH 8.0, temperature not specified in the publication
-
47
gamma-fructosyl-aminobutanoate
-
mutant K373W, pH 8.0, temperature not specified in the publication
-
0.22
Nalpha-benzyloxycarbonyl-L-lysine
pH 8.5, temperature not specified in the publication
0.51
Nalpha-benzyloxycarbonyl-L-lysine
isoform FAOD-Ao1, pH 8.5, temperature not specified in the publication
0.15
Nepsilon-fructosyl-Nalpha-benzyloxycarbonyl-L-lysine
-
wild-type, presence of 20 mM MgCl2, pH 8.0, temperature not specified in the publication
-
0.19
Nepsilon-fructosyl-Nalpha-benzyloxycarbonyl-L-lysine
-
wild-type, pH 8.0, temperature not specified in the publication
-
0.22
Nepsilon-fructosyl-Nalpha-benzyloxycarbonyl-L-lysine
-
mutant K373W, presence of 20 mM MgCl2, pH 8.0, temperature not specified in the publication
-
0.5
Nepsilon-fructosyl-Nalpha-benzyloxycarbonyl-L-lysine
-
mutant K373V, pH 8.0, temperature not specified in the publication
-
0.98
Nepsilon-fructosyl-Nalpha-benzyloxycarbonyl-L-lysine
-
mutant K373T, pH 8.0, temperature not specified in the publication
-
1.19
Nepsilon-fructosyl-Nalpha-benzyloxycarbonyl-L-lysine
-
mutant K373W, pH 8.0, temperature not specified in the publication
-
1.51
Nepsilon-fructosyl-Nalpha-benzyloxycarbonyl-L-lysine
-
mutant K373M, pH 8.0, temperature not specified in the publication
-
2.42
Nepsilon-fructosyl-Nalpha-benzyloxycarbonyl-L-lysine
-
mutant K373R, pH 8.0, temperature not specified in the publication
-
3.63
Nepsilon-fructosyl-Nalpha-benzyloxycarbonyl-L-lysine
-
wild-type, pH 7.5, temperature not specified in the publication
-
7.2
Nepsilon-fructosyl-Nalpha-benzyloxycarbonyl-L-lysine
-
mutant R94L, pH 8.0, temperature not specified in the publication
-
13.4
Nepsilon-fructosyl-Nalpha-benzyloxycarbonyl-L-lysine
-
mutant R94W, pH 8.0, temperature not specified in the publication
-
29
Nepsilon-fructosyl-Nalpha-benzyloxycarbonyl-L-lysine
-
mutant R94F, pH 8.0, temperature not specified in the publication
-
1.6
Nepsilon-fructosyl-Nalpha-t-butoxycarbonyl-L-lysine
-
amadoriase II, pH 7.4, 37°C
-
3
Nepsilon-fructosyl-Nalpha-t-butoxycarbonyl-L-lysine
-
amadoriase I, pH 7.4, 37°C
-
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
0.008
fructosyl poly-L-lysine
wild-type, pH 8, temperature not specified in the publication
-
2.91
epsilon-fructosyl-aminocaproate
-
mutant K373W, pH 8.0, temperature not specified in the publication
-
10.6
epsilon-fructosyl-aminocaproate
-
wild-type, pH 8.0, temperature not specified in the publication
-
0.007
fructosyl adamantanamine
mutant R112W, pH 8, temperature not specified in the publication
-
0.008
fructosyl adamantanamine
mutant R112Y, pH 8, temperature not specified in the publication
-
0.016
fructosyl adamantanamine
mutant R112Y/V113F/R114S, pH 8, temperature not specified in the publication
-
0.21
fructosyl adamantanamine
mutant N63D/K64Q/R112W/V113F/R114S, pH 8, temperature not specified in the publication
-
0.48
fructosyl adamantanamine
wild-type, pH 8, temperature not specified in the publication
-
2.55
fructosyl adamantanamine
mutant R112Y, pH 8, temperature not specified in the publication
-
2.9
fructosyl adamantanamine
mutant N63D/K64Q/R112W/V113F/R114S, pH 8, temperature not specified in the publication
-
5.5
fructosyl adamantanamine
mutant R112W, pH 8, temperature not specified in the publication
-
11.9
fructosyl adamantanamine
mutant R112Y/V113F/R114S, pH 8, temperature not specified in the publication
-
7.8
fructosyl glycine
mutant T60A/A188G/M244L/N257S/L261M, pH 8, 37°C
-
0.7
fructosyl L-alanine
-
mutant K373W, pH 8.0, temperature not specified in the publication
-
21
fructosyl L-alanine
-
wild-type, pH 8.0, temperature not specified in the publication
-
0.04
fructosyl L-valine
-
mutant K373W, pH 8.0, temperature not specified in the publication
-
0.15
fructosyl L-valine
-
mutant K373M, pH 8.0, temperature not specified in the publication
-
0.29
fructosyl L-valine
-
mutant K373T, pH 8.0, temperature not specified in the publication
-
0.3
fructosyl L-valine
-
mutant K373V, pH 8.0, temperature not specified in the publication
-
0.51
fructosyl L-valine
-
mutant K373R, pH 8.0, temperature not specified in the publication
-
1.3
fructosyl L-valine
-
mutant K373W, presence of 20 mM MgCl2, pH 8.0, temperature not specified in the publication
-
9.7
fructosyl L-valine
mutant T60A/A188G/M244L/N257S/L261M, pH 8, 37°C
-
10.9
fructosyl L-valine
-
wild-type, pH 8.0, temperature not specified in the publication
-
16.1
fructosyl L-valine
-
wild-type, presence of 20 mM MgCl2, pH 8.0, temperature not specified in the publication
-
18.4
fructosyl L-valine
-
mutant R94W, pH 8.0, temperature not specified in the publication
-
31.9
fructosyl L-valine
-
mutant R94F, pH 8.0, temperature not specified in the publication
-
57.7
fructosyl L-valine
-
mutant R94L, pH 8.0, temperature not specified in the publication
-
69.8
fructosyl L-valine
-
wild-type, pH 7.5, temperature not specified in the publication
-
5.8
fructosyl propylamine
</