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Information on EC 1.4.3.19 - glycine oxidase
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1.4.3.19 glycine oxidaseIUBMB Comments
A flavoenzyme containing non-covalently bound FAD. The enzyme from Bacillus subtilis is active with glycine, sarcosine, N-ethylglycine, D-alanine, D-alpha-aminobutyrate, D-proline, D-pipecolate and N-methyl-D-alanine. It differs from EC 1.4.3.3, D-amino-acid oxidase, due to its activity on sarcosine and D-pipecolate. The intermediate 2-iminoacetate is used directly by EC 2.8.1.10, thiazole synthase.
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Word Map
- 1.4.3.19
-
d-amino
- sarcosine
- flavoproteins
- glyphosate
- flavin
- fad
-
tryptophylquinone
-
flavoenzyme
-
herbicide
- d-proline
-
homotetrameric
- d-alanine
-
pseudoalteromonas
- luteoviolacea
-
protein-derived
-
thios
-
fad-dependent
-
site-saturation
-
fad-binding
-
quinoprotein
- ttq
-
half-reaction
- 5-enolpyruvylshikimate-3-phosphate
-
fad-containing
The enzyme appears in viruses and cellular organisms
Reaction Schemes
Synonyms
glycine oxidase, glyox, plgoxa, 
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SYNONYM 
ORGANISM
UNIPROT
COMMENTARY 
LITERATURE
BcGO
glycine:oxygen oxidoreductase (deaminating)
GlyOX
GO
-
-
-
-
GOX
GoxA
GoxR
LodA
PlGoxA
ThiO
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REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
2-iminoacetate + H2O = glyoxylate + NH3
(1b)
-
-
-
glycine + O2 = 2-iminoacetate + H2O2
(1a)
-
-
-
glycine + H2O + O2 = glyoxylate + NH3 + H2O2
ternary complex sequential mechanism
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glycine + H2O + O2 = glyoxylate + NH3 + H2O2
overall reaction
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-
-
glycine + H2O + O2 = glyoxylate + NH3 + H2O2
reaction mechanism involving an FADH2-imino acid complex, overview
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glycine + H2O + O2 = glyoxylate + NH3 + H2O2
reaction mechanism involving an FADH2-imino acid complex, overview
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-
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REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
oxidation
redox reaction
-
-
-
-
reduction
-
-
-
-
oxidation
-
-
-
-
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SYSTEMATIC NAME
IUBMB Comments
glycine:oxygen oxidoreductase (deaminating)
A flavoenzyme containing non-covalently bound FAD. The enzyme from Bacillus subtilis is active with glycine, sarcosine, N-ethylglycine, D-alanine, D-alpha-aminobutyrate, D-proline, D-pipecolate and N-methyl-D-alanine. It differs from EC 1.4.3.3, D-amino-acid oxidase, due to its activity on sarcosine and D-pipecolate. The intermediate 2-iminoacetate is used directly by EC 2.8.1.10, thiazole synthase.
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CAS REGISTRY NUMBER
COMMENTARY
39307-16-9
-
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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-2-aminobutyrate + H2O + O2
2-oxobutyrate + H2O2
-
as active as sarcosine
-
-
?
D-2-aminobutyrate + H2O + O2
? + NH3 + H2O2
-
2.2% of the activity with sarcosine
-
-
?
D-aminobutanoate + H2O + O2
? + H2O2
30% of the activity with sarcosine
-
-
?
D-Ile + H2O + O2
3-methyl-2-oxopentanoate + H2O2
-
about 30% of the activity with sarcosine
-
-
?
D-Leu + H2O + O2
4-methyl-2-oxopentanoate + H2O2
-
about 35% of the activity with sarcosine
-
-
?
D-Pro + H2O + O2
? + H2O2
-
about 120% of the activity with sarcosine
-
-
?
D-Val + H2O + O2
3-methyl-2-oxobutanoate + H2O2
-
about 35% of the activity with sarcosine
-
-
?
D-Val + H2O + O2
? + NH3 + H2O2
-
4.8% of the activity with sarcosine
-
-
?
N-methyl-D-Ala + H2O + O2
? + H2O2
75% of the activity with sarcosine
-
-
?
N-methyl-D-Ala + H2O + O2
? + NH3 + H2O2
-
16.9% of the activity with sarcosine
-
-
?
N-methyl-D-Ala + H2O + O2
pyruvate + methylamine + H2O2
-
about 110% of the activity with sarcosine
-
-
?
cyclopropylglycine + H2O + O2
?
enzyme is required for the biosynthesis of the thiazole moiety of thiamine diphosphate
-
-
?
D-4-hydroxyphenylglycine + H2O + O2
?
-
0.6% activity compared to glycine
-
-
?
D-4-hydroxyphenylglycine + H2O + O2
?
-
0.6% activity compared to glycine
-
-
?
D-Ala + H2O + O2
? + NH3 + H2O2
40% of the activity with sarcosine
-
-
?
D-Ala + H2O + O2
pyruvate + NH3 + H2O2
-
7.4% of the activity with sarcosine
-
-
?
D-Ala + H2O + O2
pyruvate + NH3 + H2O2
-
about 115% of the activity with sarcosine
-
-
?
D-alanine + H2O + O2
?
10% activity compared to glycine
-
-
?
D-alanine + H2O + O2
pyruvate + NH3 + H2O2
-
0.2% activity compared to glycine
-
-
?
D-alanine + H2O + O2
pyruvate + NH3 + H2O2
-
0.2% activity compared to glycine
-
-
?
D-methionine + H2O + O2
4-(methylsulfanyl)-2-oxobutanoic acid + NH3 + H2O2
25% of the activity with sarcosine
-
-
?
D-methionine + H2O + O2
4-(methylsulfanyl)-2-oxobutanoic acid + NH3 + H2O2
-
-
-
-
?
D-methionine + H2O + O2
4-(methylsulfanyl)-2-oxobutanoic acid + NH3 + H2O2
-
-
-
-
?
D-norvaline + H2O + O2
2-oxopentanoic acid + NH3 + H2O2
-
-
-
-
?
D-phenylalanine + H2O + O2
phenylpyruvate + NH3 + H2O2
-
-
-
-
?
D-pipecolate + H2O + O2
? + H2O2
-
about 85% of the activity with sarcosine
-
-
?
D-pipecolate + H2O + O2
? + H2O2
70% of the activity with sarcosine
-
-
?
D-Pro + H2O + O2
? + NH3 + H2O2
-
15.1% of the activity with sarcosine
-
-
?
D-Pro + H2O + O2
? + NH3 + H2O2
110% of the activity with sarcosine
-
-
?
D-proline + H2O + O2
?
-
0.3% activity compared to glycine
-
-
?
D-proline + H2O + O2
?
25% activity compared to glycine
-
-
?
D-valine + H2O + O2
3-methyl-2-oxobutanoic acid + NH3 + H2O2
-
-
-
-
?
D-valine + H2O + O2
3-methyl-2-oxobutanoic acid + NH3 + H2O2
-
-
-
-
?
glycine + H2O + O2
glyoxylate + NH3 + H2O2
-
-
-
-
?
glycine + H2O + O2
glyoxylate + NH3 + H2O2
-
free glycine oxidase forms the anionic red semiquinone upon photoreduction.This species is thermodynamically stable, as indicated by the large separation of the two single-electron reduction potentials of DeltaE 290 mV. The first potential is pH-independent, while the second is dependent. The midpoint reduction potential exhibits a 23.4 mV/pH unit slope, which is consistent with an overall two-electrons/one-proton transfer in the reduction to yield anionic reduced flavin. In the presence of glycolate and at pH 7.5 the potential for the semiquinone-reduced enzyme couple is shifted positively by about 160 mV, this favors a two-electron transfer compared to the free enzyme. Binding of glycolate and sulfite is also affected by pH
-
?
glycine + H2O + O2
glyoxylate + NH3 + H2O2
-
77.4% of the activity with sarcosine
-
-
?
glycine + H2O + O2
glyoxylate + NH3 + H2O2
85% of the activity with sarcosine
-
-
?
glycine + H2O + O2
glyoxylate + NH3 + H2O2
-
-
-
?
glycine + H2O + O2
glyoxylate + NH3 + H2O2
-
100% activity
-
-
?
glycine + H2O + O2
glyoxylate + NH3 + H2O2
-
-
-
?
glycine + H2O + O2
glyoxylate + NH3 + H2O2
-
-
-
?
glycine + O2 + H2O
glyoxylate + H2O2 + NH3
-
using samples of [2-RS-3H2,2-14C]-, [2-R-3H,2-14C]-, and [2-S-3H,2-14C]glycine, HSi is removed in the overall process. Incubation of the enzyme with [2-RS-3H2,2-14C]glycine under anaerobic conditions, when only the reducing half of the reaction can occur, leads to the recovery of 98.5% of the original glycine, which has the same 3H:14C ratio as the starting substrate. Isotope effects, overview
-
-
?
glycine + O2 + H2O
glyoxylate + H2O2 + NH3
-
using samples of [2-RS-3H2,2-14C]-, [2-R-3H,2-14C]-, and [2-S-3H,2-14C]glycine, HSi is removed in the overall process. Incubation of the enzyme with [2-RS-3H2,2-14C]glycine under anaerobic conditions, when only the reducing half of the reaction can occur, leads to the recovery of 98.5% of the original glycine, which has the same 3H:14C ratio as the starting substrate. Isotope effects, overview
-
-
?
glycine ethyl ester + H2O + O2
?
-
30.7% activity compared to glycine
-
-
?
glycine ethyl ester + H2O + O2
?
5% activity compared to glycine
-
-
?
glycine ethyl ester + H2O + O2
?
5% activity compared to glycine
-
-
?
glycine-ethyl-ester + H2O + O2
? + H2O2
90% of the activity with sarcosine
-
-
?
glyphosate + H2O + O2
?
the wild type enzyme shows very low activity with glyphosate
-
-
?
glyphosate + H2O + O2
? + H2O2
110% of the activity with sarcosine
-
-
?
glyphosate + H2O + O2
glyoxylate + aminomethylphosphonic acid + NH3 + H2O2
-
-
-
?
glyphosate + H2O + O2
glyoxylate + aminomethylphosphonic acid + NH3 + H2O2
-
-
-
?
N-ethylglycine + H2O + O2
?
-
0.3% activity compared to glycine
-
-
?
N-ethylglycine + H2O + O2
glyoxylate + ethylamine + H2O2
-
85.3% of the activity with sarcosine
-
-
?
N-ethylglycine + H2O + O2
glyoxylate + ethylamine + H2O2
-
about 65% of the activity with sarcosine
-
-
?
N-ethylglycine + H2O + O2
glyoxylate + ethylamine + H2O2
120% of the activity with sarcosine
-
-
?
N-ethylglycine + H2O + O2
glyoxylate + ethylamine + H2O2
-
-
-
-
?
sarcosine + H2O + O2
?
-
0.1% activity compared to glycine
-
-
?
sarcosine + H2O + O2
glyoxylate + methylamine + H2O2
-
-
-
-
?