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Information on EC 2.3.1.13 - glycine N-acyltransferase
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2.3.1.13 glycine N-acyltransferaseIUBMB Comments
The CoA derivatives of a number of aliphatic and aromatic acids, but not phenylacetyl-CoA or (indol-3-yl)acetyl-CoA, can act as donor. Not identical with EC 2.3.1.68 glutamine N-acyltransferase or EC 2.3.1.71 glycine N-benzoyltransferase.
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Word Map
The expected taxonomic range for this enzyme is: Eukaryota, Bacteria
Synonyms
glyat, glyatl1, glycine n-acyltransferase, glycine-n-acylase, glycine-n-acyltransferase, acyl-coa:glycine n-acyltransferase, glycine acyltransferase, glyatl3, glyatl2, glycine-n-acyltransferase like 1, 
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SYNONYM 
ORGANISM
UNIPROT
COMMENTARY 
LITERATURE
acyltransferase, glycine
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GlyAT
GLYATL1
glycine acyltransferase
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glycine-N-acylase
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-
-
-
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REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
acyl-CoA + glycine = CoA + N-acylglycine
sequential reaction mechanism, acyl-CoA substrate adds to the enzyme first, glycine adds before CoA leaves and the peptide product dissociates last
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acyl-CoA + glycine = CoA + N-acylglycine
residue Glu226 functions to deprotonate glycine, facilitating nucleophilic attack on the acyl-CoA substrate
acyl-CoA + glycine = CoA + N-acylglycine
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SYSTEMATIC NAME
IUBMB Comments
acyl-CoA:glycine N-acyltransferase
The CoA derivatives of a number of aliphatic and aromatic acids, but not phenylacetyl-CoA or (indol-3-yl)acetyl-CoA, can act as donor. Not identical with EC 2.3.1.68 glutamine N-acyltransferase or EC 2.3.1.71 glycine N-benzoyltransferase.
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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
benzoyl-CoA + glycine ethyl ester
CoA + N-benzoylglycine ethyl ester
-
-
-
?
benzoyl-CoA + glycine methyl ester
CoA + N-benzoylglycine methyl ester
-
-
-
?
heptanoyl-CoA + glycine
CoA + N-heptanoylglycine
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3.9% of activity with benzoyl-coA
-
?
acyl-CoA + glycine
CoA + N-acylglycine
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phenylacetyl-CoA or indoleacetyl-CoA can not act as acyl donor
-
?
acyl-CoA + glycine
CoA + N-acylglycine
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phenylacetyl-CoA or indoleacetyl-CoA can not act as acyl donor
-
?
acyl-CoA + glycine
CoA + N-acylglycine
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the CoA derivatives of a number of aliphatic and aromatic acids, e.g. benzoyl-CoA and butyryl-CoA can act as acyl donor
-
?
acyl-CoA + glycine
CoA + N-acylglycine
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salicyl-CoA acts as acyl donor
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?
acyl-CoA + glycine
CoA + N-acylglycine
-
the CoA derivatives of a number of aliphatic and aromatic acids, e.g. benzoyl-CoA and butyryl-CoA can act as acyl donor
-
?
acyl-CoA + glycine
CoA + N-acylglycine
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salicyl-CoA acts as acyl donor
-
?
acyl-CoA + glycine
CoA + N-acylglycine
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phenylacetyl-CoA acts as acyl donor
-
?
acyl-CoA + glycine
CoA + N-acylglycine
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the CoA derivatives of a number of aliphatic and aromatic acids, e.g. benzoyl-CoA and butyryl-CoA can act as acyl donor
-
?
acyl-CoA + glycine
CoA + N-acylglycine
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phenylacetyl-CoA acts as acyl donor
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?
acyl-CoA + glycine
CoA + N-acylglycine
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enzyme is believed to catalyze the formation of both the straight-chain and branched-chain acylglycines from the corresponding acyl-CoA esters
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?
benzoyl-CoA + glycine
CoA + N-benzoylglycine
best substrates are benzoyl-CoA as an acyl donor and glycine as acyl acceptor
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-
?
benzoyl-CoA + glycine
CoA + N-benzoylglycine
best substrate combination
i.e. hippurate
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?
benzoyl-CoA + glycine
CoA + N-benzoylglycine
glycine serves as the best amino donor substrate, and benzoyl-CoA serves as the best the amino acceptor substrate
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-
?
benzoyl-CoA + L-glutamine
CoA + N-benzoyl-L-glutamine
24% of the rate with glycine and benzoyl-CoA
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-
?
butyryl-CoA + glycine
CoA + N-butyrylglycine
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19% of activity with benzoyl-coA
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?
isovaleryl-CoA + glycine
CoA + N-isovalerylglycine
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8.4% of activity with benzoyl-coA
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?
salicyl-CoA + glycine
CoA + salicyluric acid
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15% of activity with benzoyl-coA
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?
additional information
?
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substrates are medium- and long-chain acyl-CoAs ranging from chain-length C8:0-CoA to C18:0-CoA. Enzyme is specific for glycine as an acceptor molecule, and preferentially produces N-oleoyl glycine. No substrates: docosahexanoyl-CoA and chenodeoxycholoyl-CoA, L-alanine, l-serine
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?
additional information
?
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GLYAT exhibits mechanistic kinetic cooperativity
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additional information
?
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GLYAT exhibits mechanistic kinetic cooperativity
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additional information
?
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enzyme also shows glycine N-benzoyltransferase activity, reaction of EC 2.3.1.71. Amino acceptor substrate preference in decreasing order is benzoyl-CoA, butyryl-CoA, hexanoyl-CoA, acetyl-CoA
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-
?
additional information
?
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enzyme also shows glycine N-benzoyltransferase activity, reaction of EC 2.3.1.71. Amino acceptor substrate preference in decreasing order is benzoyl-CoA, butyryl-CoA, hexanoyl-CoA, acetyl-CoA
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-
?
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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
acyl-CoA + glycine
CoA + N-acylglycine
-
enzyme is believed to catalyze the formation of both the straight-chain and branched-chain acylglycines from the corresponding acyl-CoA esters
-
?
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METALS and IONS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
p-chloromercuribenzoate
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1 mM, 90% inhibition after 40 min, 20% activity can be recovered by adding 20fold excess of dithiothreitol, benzoyl-CoA protects
additional information
not inhibited by alanine, beta-alanine, valine, and threonine
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additional information
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not inhibited by alanine, beta-alanine, valine, and threonine
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DISEASE
TITLE OF PUBLICATION
LINK TO PUBMED
Breast Neoplasms
Downregulation of GLYAT Facilitates Tumor Growth and Metastasis and Poor Clinical Outcomes Through the PI3K/AKT/Snail Pathway in Human Breast Cancer.
Carcinogenesis
Designation of enzyme activity of glycine-N-acyltransferase family genes and depression of glycine-N-acyltransferase in human hepatocellular carcinoma.
Carcinoma, Hepatocellular
Designation of enzyme activity of glycine-N-acyltransferase family genes and depression of glycine-N-acyltransferase in human hepatocellular carcinoma.
Carcinoma, Hepatocellular
The expression and prognostic value of GLYATL1 and its potential role in hepatocellular carcinoma.
Hyperglycinemia, Nonketotic
Glycine and benzoate conjugation and glycine acyltransferase activity in the developing and adult rat: possible relationships to nonketotic hyperglycinemia.
Metabolism, Inborn Errors
Frequent sequence variants of human glycine N-acyltransferase (GLYAT) and inborn errors of metabolism.
Neoplasm Metastasis
Downregulation of GLYAT Facilitates Tumor Growth and Metastasis and Poor Clinical Outcomes Through the PI3K/AKT/Snail Pathway in Human Breast Cancer.
Neoplasms
Characterization of glycine-N-acyltransferase like 1 (GLYATL1) in prostate cancer.
Neoplasms
Downregulation of GLYAT Facilitates Tumor Growth and Metastasis and Poor Clinical Outcomes Through the PI3K/AKT/Snail Pathway in Human Breast Cancer.
Neoplasms
Glycine conjugation: importance in metabolism, the role of glycine N-acyltransferase, and factors that influence interindividual variation.
Neoplasms
Overexpression of lipid metabolism genes and PBX1 in the contralateral breasts of women with estrogen receptor-negative breast cancer.
Neoplasms
The expression and prognostic value of GLYATL1 and its potential role in hepatocellular carcinoma.
Porphyrias
The role of substrates for glycine acyltransferase, and the role of sulfanilamide and acetate in the reversal of chemically-induced porphyria in the rat.
Prostatic Neoplasms
Characterization of glycine-N-acyltransferase like 1 (GLYATL1) in prostate cancer.
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KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
9.7
glycine ethyl ester
apparent value, at pH 8.0, temperature not specified in the publication
29
Glycine methyl ester
apparent value, at pH 8.0, temperature not specified in the publication
0.0044
oleoyl-CoA
pH not specified in the publication, temperature not specified in the publication
0.209
acetyl-CoA
apparent value, at pH 8.0, temperature not specified in the publication
0.0094
benzoyl-CoA
apparent value, at pH 8.0, temperature not specified in the publication
0.038
benzoyl-CoA
mutant enzyme N156S, apparent value, at pH 8.0 and 37°C
0.053
benzoyl-CoA
mutant enzyme F168L, apparent value, at pH 8.0 and 37°C
0.071
benzoyl-CoA
mutant enzyme R131H, apparent value, at pH 8.0 and 37°C
30.42
benzoyl-CoA
K0.5 value at 2.5 mM gylcine, pH 8.0, temperature not specified in the publication
108.3
benzoyl-CoA
K0.5 value at 5 mM gylcine, pH 8.0, temperature not specified in the publication
305
benzoyl-CoA
K0.5 value at 20 mM gylcine, pH 8.0, temperature not specified in the publication
0.052
butyryl-CoA
apparent value, at pH 8.0, temperature not specified in the publication
2.189
glycine
K0.5 value at 0.02 mM benzoyl-CoA, pH 8.0, temperature not specified in the publication
2.326
glycine
K0.5 value at 0.04 mM benzoyl-CoA, pH 8.0, temperature not specified in the publication
2.956
glycine
K0.5 value at 0.08 mM benzoyl-CoA, pH 8.0, temperature not specified in the publication
6.1
glycine
apparent value, at pH 8.0, temperature not specified in the publication
450
hexanoyl-CoA
apparent value, at pH 8.0, temperature not specified in the publication
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TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
3.2
glycine
apparent value, at pH 8.0, temperature not specified in the publication
0.57
glycine ethyl ester
apparent value, at pH 8.0, temperature not specified in the publication
1
Glycine methyl ester
apparent value, at pH 8.0, temperature not specified in the publication
0.8
acetyl-CoA
apparent value, at pH 8.0, temperature not specified in the publication
4.2
benzoyl-CoA
apparent value, at pH 8.0, temperature not specified in the publication
15
butyryl-CoA
apparent value, at pH 8.0, temperature not specified in the publication
4.6
hexanoyl-CoA
apparent value, at pH 8.0, temperature not specified in the publication
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kcat/KM VALUE [1/mMs-1]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
0.52
glycine
apparent value, at pH 8.0, temperature not specified in the publication
0.059
glycine ethyl ester
apparent value, at pH 8.0, temperature not specified in the publication
0.035
Glycine methyl ester
apparent value, at pH 8.0, temperature not specified in the publication
3.8
acetyl-CoA
apparent value, at pH 8.0, temperature not specified in the publication
450
benzoyl-CoA
apparent value, at pH 8.0, temperature not specified in the publication
290
butyryl-CoA
apparent value, at pH 8.0, temperature not specified in the publication
100
hexanoyl-CoA
apparent value, at pH 8.0, temperature not specified in the publication
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Ki VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
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IC50 VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
58
glycolic acid
Mus musculus
apparent value, at pH 8.0, temperature not specified in the publication