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Information on EC 4.3.2.8 - gamma-glutamylamine cyclotransferase
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EC Tree
4.3.2.8 gamma-glutamylamine cyclotransferaseIUBMB Comments
The enzyme, found in vertebrates, has no activity toward alpha-(gamma-L-glutamyl)-L-amino acids (cf. EC 4.3.2.9, gamma-glutamylcyclotransferase). The enzyme acts as a cyclotransferase, cleaving the amide bond via transamidation using the alpha-amine of the gamma-L-glutamyl residue, releasing it as the cyclic 5-oxo-L-proline.
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Word Map
- 4.3.2.8
-
transglutaminase-catalyzed
- putrescine
- polyamine
-
alpha-amino
-
crosslinks
-
disassembly
- spermine
-
isodipeptide
- amide
- transglutaminases
- analysis
The expected taxonomic range for this enzyme is: Eukaryota, Bacteria
Synonyms
gamma-glutamylamine cyclotransferase, 
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SYNONYM 
ORGANISM
UNIPROT
COMMENTARY 
LITERATURE
GGACT
GGACT
-
-
-
-
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REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
epsilon-(gamma-L-glutamyl)-L-lysine = L-lysine + 5-oxo-L-proline
-
-
-
-
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SYSTEMATIC NAME
IUBMB Comments
epsilon-(gamma-L-glutamyl)-L-lysine gamma-glutamyl cyclotransferase (5-oxo-L-proline producing)
The enzyme, found in vertebrates, has no activity toward alpha-(gamma-L-glutamyl)-L-amino acids (cf. EC 4.3.2.9, gamma-glutamylcyclotransferase). The enzyme acts as a cyclotransferase, cleaving the amide bond via transamidation using the alpha-amine of the gamma-L-glutamyl residue, releasing it as the cyclic 5-oxo-L-proline.
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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
alpha-N-acetyl-epsilon-(L-gamma-glutamyl)-L-lysine methyl ester
alpha-N-acetyl-L-lysine + 5-oxo-L-proline
-
-
-
-
?
epsilon-(gamma-L-glutamyl)-D-lysine
D-lysine + 5-oxo-L-proline
-
-
-
-
?
L-gamma-glutamyl-(2S)-2-methylbutylamine
(2S)-2-methylbutylamine + 5-oxo-L-proline
-
-
-
-
?
L-gamma-glutamyl-2-methylbutylamine
2-methylbutylamine + 5-oxo-L-proline
-
-
-
-
?
L-gamma-glutamyl-n-butylamine
n-butylamine + 5-oxo-L-proline
-
-
-
-
?
L-gamma-glutamyl-n-propylamine
n-propylamine + 5-oxo-L-proline
-
-
-
-
?
L-gamma-glutamylcyclopentylamine
cyclopentylamine + 5-oxo-L-proline
-
-
-
-
?
L-gamma-glutamylneohexylamine
neohexylamine + 5-oxo-L-proline
-
-
-
-
?
L-gamma-glutamylputrescine
putrescine + 5-oxo-L-proline
-
-
-
-
?
Nepsilon-(L-gamma-glutamyl)-D-lysine
D-lysine + 5-oxo-L-proline
-
-
-
-
?
Nepsilon-(L-gamma-glutamyl)-L-lysine
L-lysine + 5-oxo-L-proline
-
-
-
-
?
epsilon-(gamma-L-glutamyl)-L-lysine
L-lysine + 5-oxo-L-proline
-
-
-
-
?
additional information
?
-
no substrates: L-gamma-glutamyl-alpha-amino acid substrates such as L-gamma-glutamyl-L-alpha-cysteine and L-gamma-glutamyl-L-alpha-alanine
-
-
?
additional information
?
-
-
enzyme does not act on most gamma-glutamyl-alpha-amino acids, nor is it active toward the epsilon-lysyl derivatives of L-aspartic acid or D-glutamic acid or on derivatives of epsilon-(L-gamma-glutamyl)-L-lysine in which the alpha-amino or the alpha-carboxyl function of the glutamyl moiety is blocked
-
-
?
additional information
?
-
-
introduction of a methyl or carboxylate group on the carbon adjacent to the side-chain amide nitrogen in L-gamma-glutamylamine substrates results in a dramatic decrease in activity
-
-
?
additional information
?
-
-
no activity toward alpha-(gamma-L-glutamyl)-L-amino acids or on epsilon-(D-gamma-glutamyl)-L-lysine, epsilon-(L-beta-aspartyl)-L-lysine, epsilon-(D,L-beta-aminoglutaryl)-L-lysine, L-glutamine, alpha-N-acetyl-epsilon-[L-alpha-glutamylglycine]-L-lysine methyl ester, alpha-N-acetyl-epsilon-(gamma-L-alpha-glutamyl-L-valine ethyl ester)-L-lysine methyl ester, N-[gamma-(L-alpha-glutamylglycylglycylglycine)]isobutylamine, epsilon-acetyl-L-lysine, epsilon-formyl-L-lysine, and L-gamma-glutamyl-p-nitroanilide
-
-
?
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NATURAL SUBSTRATE
NATURAL 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
epsilon-(gamma-L-glutamyl)-L-lysine
L-lysine + 5-oxo-L-proline
-
-
-
-
?
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INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
additional information
-
no inhibition by other modification reagents or other divalent cations
-
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KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
0.011
gamma-glutamyldansylcadaverine
-
pH not specified in the publication, temperature not specified in the publication
0.38
L-gamma-glutamyl-(2S)-2-methylbutylamine
-
pH not specified in the publication, temperature not specified in the publication
0.38
L-gamma-glutamyl-2-methylbutylamine
-
pH not specified in the publication, temperature not specified in the publication
0.91
L-gamma-glutamyl-beta-alanine
-
pH not specified in the publication, temperature not specified in the publication
0.25
L-gamma-glutamyl-n-butylamine
-
pH not specified in the publication, temperature not specified in the publication
0.32
L-gamma-glutamyl-n-propylamine
-
pH not specified in the publication, temperature not specified in the publication
0.56
L-gamma-glutamylbenzylamine
-
pH not specified in the publication, temperature not specified in the publication
0.084
L-gamma-glutamylcyclopentylamine
-
pH not specified in the publication, temperature not specified in the publication
0.011
L-gamma-glutamyldansylcadaverine
-
pH 8.6, pH not specified in the publication, temperature not specified in the publication
0.12
L-gamma-glutamylneohexylamine
-
pH not specified in the publication, temperature not specified in the publication
0.27
Nepsilon-(L-gamma-glutamyl)-D-lysine
-
pH not specified in the publication, temperature not specified in the publication
0.26
Nepsilon-(L-gamma-glutamyl)-L-lysine
-
pH not specified in the publication, temperature not specified in the publication
0.19
S-(cyclohexylamine)-L-cysteine
-
pH not specified in the publication, temperature not specified in the publication
0.091
S-(n-butylcarbamyl)-L-cysteine
-
pH not specified in the publication, temperature not specified in the publication
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TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
0.21
L-gamma-glutamyl-(2S)-2-methylbutylamine
-
pH not specified in the publication, temperature not specified in the publication
0.19
L-gamma-glutamyl-2-methylbutylamine
-
pH not specified in the publication, temperature not specified in the publication
0.18
L-gamma-glutamyl-beta-alanine
-
pH not specified in the publication, temperature not specified in the publication
0.21
L-gamma-glutamyl-n-butylamine
-
pH not specified in the publication, temperature not specified in the publication
0.23
L-gamma-glutamyl-n-propylamine
-
pH not specified in the publication, temperature not specified in the publication
0.4
L-gamma-glutamylbenzylamine
-
pH not specified in the publication, temperature not specified in the publication
0.076
L-gamma-glutamylcyclopentylamine
-
pH not specified in the publication, temperature not specified in the publication
0.18
L-gamma-glutamylneohexylamine
-
pH not specified in the publication, temperature not specified in the publication
0.25
Nepsilon-(L-gamma-glutamyl)-D-lysine
-
pH not specified in the publication, temperature not specified in the publication
0.2
Nepsilon-(L-gamma-glutamyl)-L-lysine
-
pH not specified in the publication, temperature not specified in the publication
0.26
S-(cyclohexylamine)-L-cysteine
-
pH not specified in the publication, temperature not specified in the publication
0.27
S-(n-butylcarbamyl)-L-cysteine
-
pH not specified in the publication, temperature not specified in the publication
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kcat/KM VALUE [1/mMs-1]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
0.55
L-gamma-glutamyl-(2S)-2-methylbutylamine
-
pH not specified in the publication, temperature not specified in the publication
0.51
L-gamma-glutamyl-2-methylbutylamine
-
pH not specified in the publication, temperature not specified in the publication
0.19
L-gamma-glutamyl-beta-alanine
-
pH not specified in the publication, temperature not specified in the publication
0.83
L-gamma-glutamyl-n-butylamine
-
pH not specified in the publication, temperature not specified in the publication
0.72
L-gamma-glutamyl-n-propylamine
-
pH not specified in the publication, temperature not specified in the publication
0.71
L-gamma-glutamylbenzylamine
-
pH not specified in the publication, temperature not specified in the publication
0.9
L-gamma-glutamylcyclopentylamine
-
pH not specified in the publication, temperature not specified in the publication
1.45
L-gamma-glutamylneohexylamine
-
pH not specified in the publication, temperature not specified in the publication
0.92
Nepsilon-(L-gamma-glutamyl)-D-lysine
-
pH not specified in the publication, temperature not specified in the publication
0.78
Nepsilon-(L-gamma-glutamyl)-L-lysine
-
pH not specified in the publication, temperature not specified in the publication
1.5
S-(cyclohexylamine)-L-cysteine
-
pH not specified in the publication, temperature not specified in the publication
2.8
S-(n-butylcarbamyl)-L-cysteine
-
pH not specified in the publication, temperature not specified in the publication
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pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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pH RANGE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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ORGANISM
COMMENTARY
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
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SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
SOURCE
-
protein is already present at the dormant stage and gradually activated during germination in soybean seeds
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MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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SUBUNIT
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
monomer
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CRYSTALLIZATION (Commentary)
ORGANISM
UNIPROT
LITERATURE
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PROTEIN VARIANTS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
E82A
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PURIFICATION (Commentary)
ORGANISM
UNIPROT
LITERATURE
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CLONED (Commentary)
ORGANISM
UNIPROT
LITERATURE
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APPLICATION
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
analysis
endpoint-assay, L-lysine is converted to alpha-keto epsilon-aminocaproate semicarbazone in the presence of semicarbazide, excess L-lysine alpha-oxidase, and catalase
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REF.
AUTHORS
TITLE
JOURNAL
VOL.
PAGES
YEAR
ORGANISM (UNIPROT)
PUBMED ID
SOURCE
Bowser, T.E.; Trawick, M.L.
Probing the specificity of gamma-glutamylamine cyclotransferase an enzyme involved in the metabolism of transglutaminase-catalyzed protein crosslinks
Amino Acids
44
143-150
2013
Oryctolagus cuniculus
brenda
Danson, J.W.; Trawick, M.L.; Cooper, A.J.
Spectrophotometric assays for L-lysine alpha-oxidase and gamma-glutamylamine cyclotransferase
Anal. Biochem.
303
120-130
2002
Bos taurus (Q0VFX9), Bos taurus
brenda
Kang, H.; Lee, S.G.; Cho, Y.D.
Identification of glycinin in vivo as a polyamine-conjugated protein via a gamma-glutamyl linkage
Biochem. J.
332
467-473
1998
Glycine max
brenda
Kang, H.; Park, S.; Cho, Y.
Identification of gamma-glutamylamine cyclotransferase, as the preform enzyme at the dormant stage, from soybean (Glycine max) seeds
J. Biochem. Mol. Biol.
30
438-442
1997
Glycine max
-
brenda
Oakley, A.J.; Coggan, M.; Board, P.G.
Identification and characterization of gamma-glutamylamine cyclotransferase, an enzyme responsible for gamma-glutamyl-epsilon-lysine catabolism
J. Biol. Chem.
285
9642-9648
2010
Homo sapiens (Q9BVM4)
brenda
Fink, M.; Folk, J.
gamma-Glutamylamine cyclotransferase - an enzyme involved in the catabolism of epsilon-(gamma-glutamyl)lysine and other gamma-glutamylamines
Mol. Cell. Biochem.
38
59-67
1981
Oryctolagus cuniculus
brenda
Fink, M.L.; Chung, S.I.; Folk, J.E.
gamma-Glutamylamine cyclotransferase specificity toward epsilon-(L-gamma-glutamyl)-L-lysine and related compounds
Proc. Natl. Acad. Sci. USA
77
4564-4568
1980
Oryctolagus cuniculus
brenda
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