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Information on EC 2.3.1.87 - aralkylamine N-acetyltransferase and Organism(s) Ovis aries and UniProt Accession Q29495

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IUBMB Comments
Narrow specificity towards 2-arylethylamines, including serotonin (5-hydroxytryptamine), tryptamine, 5-methoxytryptamine and phenylethylamine. This is the penultimate enzyme in the production of melatonin (5-methoxy-N-acetyltryptamine) and controls its synthesis (cf. EC 2.1.1.4, acetylserotonin O-methyltransferase). Differs from EC 2.3.1.5 arylamine N-acetyltransferase.
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Select one or more organisms in this record:
This record set is specific for:
Ovis aries
UNIPROT: Q29495
Word Map
The taxonomic range for the selected organisms is: Ovis aries
The enzyme appears in selected viruses and cellular organisms
Synonyms
AA-NAT, AANAT, AANAT1, AANAT2, AANATL7, AATNATL2, acetyl-CoA:aralkylamine N-acetyltransferase, acetyltransferase, arylalkylamine N-, arylalkylamine N-acetyltransferase, arylalkylamine N-acetyltransferase 1, more
SYNONYM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
AA-NAT
-
-
-
-
AANAT
acetyl-CoA:aralkylamine N-acetyltransferase
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-
-
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acetyltransferase, arylalkylamine N-
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-
-
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arylalkylamine N-acetyltransferase
-
-
-
-
N-acetyltransferase
-
-
-
-
oAANAT
271
-
serotonin acetylase
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-
-
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serotonin acetyltransferase
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-
-
-
additional information
271
AANAT is a member of the GCN5-related N-acetyltransferase, GNAT, superfamily of acetyltransferases
REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
acetyl-CoA + a 2-arylethylamine = CoA + an N-acetyl-2-arylethylamine
show the reaction diagram
REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
Acyl group transfer
-
-
-
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PATHWAY SOURCE
PATHWAYS
SYSTEMATIC NAME
IUBMB Comments
acetyl-CoA:2-arylethylamine N-acetyltransferase
Narrow specificity towards 2-arylethylamines, including serotonin (5-hydroxytryptamine), tryptamine, 5-methoxytryptamine and phenylethylamine. This is the penultimate enzyme in the production of melatonin (5-methoxy-N-acetyltryptamine) and controls its synthesis (cf. EC 2.1.1.4, acetylserotonin O-methyltransferase). Differs from EC 2.3.1.5 arylamine N-acetyltransferase.
CAS REGISTRY NUMBER
COMMENTARY hide
92941-56-5
-
SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
acetyl-CoA + tryptamine
CoA + N-acetyltryptamine
show the reaction diagram
-
-
-
-
?
acetyl-CoA + 2,5-dimethoxyphenylethylamine
CoA + N-acetyl-2,5-dimethoxyphenylethylamine
show the reaction diagram
-
68% of the activity with 2-phenylethylamine
-
-
?
acetyl-CoA + 2-(2,3-dichlorophenyl)-ethylamine
CoA + N-acetyl-2-(2,3-dichlorophenyl)-ethylamine
show the reaction diagram
-
84% of the activity with 2-phenylethylamine
-
-
?
acetyl-CoA + 2-(2-chlorophenyl)-ethylamine
CoA + N-acetyl-2-(2-chlorophenyl)-ethylamine
show the reaction diagram
-
102% of the activity with 2-phenylethylamine
-
-
?
acetyl-CoA + 2-(3,4-dihydroxyphenyl)-ethylamine
CoA + N-acetyl-2-(3,4-dihydroxyphenyl)-ethylamine
show the reaction diagram
-
64% of the activity with 2-phenylethylamine
-
-
?
acetyl-CoA + 2-(3,4-dimethoxyphenyl)-ethylamine
CoA + N-acetyl-2-(3,4-dimethoxyphenyl)-ethylamine
show the reaction diagram
-
15% of the activity with 2-phenylethylamine
-
-
?
acetyl-CoA + 2-(3-chlorophenyl)-ethylamine
CoA + N-acetyl-2-(3-chlorophenyl)-ethylamine
show the reaction diagram
-
110% of the activity with 2-phenylethylamine
-
-
?
acetyl-CoA + 2-(3-fluorophenyl)-ethylamine
CoA + N-acetyl-2-(3-fluorophenyl)-ethylamine
show the reaction diagram
-
93% of the activity with 2-phenylethylamine
-
-
?
acetyl-CoA + 2-(4-bromophenyl)-ethylamine
CoA + N-acetyl-2-(4-bromophenyl)-ethylamine
show the reaction diagram
-
87% of the activity with 2-phenylethylamine
-
-
?
acetyl-CoA + 2-(4-chlorophenyl)ethylamine
CoA + N-acetyl-2-(4-chlorophenyl)ethylamine
show the reaction diagram
-
91% of the activity with 2-phenylethylamine
-
-
?
acetyl-CoA + 2-(4-fluorophenyl)-ethylamine
CoA + N-acetyl-2-(4-fluorophenyl)-ethylamine
show the reaction diagram
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60% of the activity with 2-phenylethylamine
-
-
?
acetyl-CoA + 2-(p-fluorophenyl)-ethylamine
CoA + N-acetyl-2-(p-fluorophenyl)-ethylamine
show the reaction diagram
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as active as with 2-phenylethylamine
-
-
?
acetyl-CoA + 2-(p-nitrophenyl)-ethylamine
CoA + N-acetyl-2-(p-nitrophenyl)-ethylamine
show the reaction diagram
-
53% of the activity with 2-phenylethylamine
-
-
?
acetyl-CoA + 2-(p-tolyl)-ethylamine
CoA + N-acetyl-2-(p-tolyl)-ethylamine
show the reaction diagram
-
87% of the activity with 2-phenylethylamine
-
-
?
acetyl-CoA + 2-fluorophenylethylamine
CoA + N-acetyl-2-fluorophenylethylamine
show the reaction diagram
-
52% of the activity with 2-phenylethylamine
-
-
?
acetyl-CoA + 2-methoxyphenylethylamine
CoA + N-acetyl-2-methoxyphenylethylamine
show the reaction diagram
-
97% of the activity with 2-phenylethylamine
-
-
?
acetyl-CoA + 2-phenylethylamine
CoA + N-acetyl-2-phenylethylamine
show the reaction diagram
-
-
-
-
?
acetyl-CoA + 3-hydroxy-4-methoxyphenethylamine
CoA + N-acetyl-3-hydroxy-4-methoxyphenethylamine
show the reaction diagram
-
7.2% of the activity with 2-phenylethylamine
-
-
?
acetyl-CoA + 3-hydroxyphenethylamine
CoA + N-acetyl-3-hydroxyphenethylamine
show the reaction diagram
-
36% of the activity with 2-phenylethylamine
-
-
?
acetyl-CoA + 3-indolebutylamine
CoA + N-acetyl-(3-indol-3-yl-butyl)-amine
show the reaction diagram
-
60-fold less efficiently than serotonin
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-
?
acetyl-CoA + 3-indolepropylamine
CoA + N-acetyl-(3-indol-3-yl-propyl)-amine
show the reaction diagram
-
20-fold less efficiently than serotonin
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-
?
acetyl-CoA + 3-methoxy-2-phenylethylamine
CoA + N-acetyl-3-methoxy-2-phenylethylamine
show the reaction diagram
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55% of the activity with 2-phenylethylamine
-
-
?
acetyl-CoA + 3-methoxytyramine
CoA + N-acetyl-3-methoxytyramine
show the reaction diagram
-
73% of the activity with 2-phenylethylamine
-
-
?
acetyl-CoA + 4-(2-aminoethyl)-benzenesulfonamide
CoA + ?
show the reaction diagram
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1% of the activity with 2-phenylethylamine
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-
?
acetyl-CoA + 4-(2-aminoethyl)-benzenesulfonyl fluoride
CoA + ?
show the reaction diagram
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7.4% of the activity with 2-phenylethylamine
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-
?
acetyl-CoA + 4-methoxyphenylethylamine
CoA + N-acetyl-4-methoxyphenylethylamine
show the reaction diagram
-
10% of the activity with 2-phenylethylamine
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-
?
acetyl-CoA + 5-hydroxydopamine
CoA + N-acetyl-5-hydroxydopamine
show the reaction diagram
-
4.4% of the activity with 2-phenylethylamine
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-
?
acetyl-CoA + 5-methoxytryptamine
CoA + N-acetyl-5-methoxytryptamine
show the reaction diagram
-
-
-
-
?
acetyl-CoA + 6-fluorotryptamine
CoA + N-acetyl-6-fluorotryptamine
show the reaction diagram
-
-
-
-
?
acetyl-CoA + 6-hydroxydopamine
CoA + N-acetyl-6-hydroxydopamine
show the reaction diagram
-
1.5% of the activity with 2-phenylethylamine
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?
acetyl-CoA + alpha-methyltryptamine
CoA + N-acetyl-alpha-methyltryptamine
show the reaction diagram
-
racemic, 9:1 stereoselectivity for R-enantiomer, less efficiently than serotonin
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-
?
acetyl-CoA + beta-phenylethylamine
CoA + N-(2-phenylethyl)-acetaminde
show the reaction diagram
-
-
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?
acetyl-CoA + Nomega-methyltryptamine
CoA + ?
show the reaction diagram
-
less efficiently than serotonin
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?
acetyl-CoA + serotonin
CoA + N-acetylserotonin
show the reaction diagram
acetyl-CoA + tryptamine
CoA + N-acetyltryptamine
show the reaction diagram
acetyl-CoA + tryptamine
N-acetyltryptamine + CoA
show the reaction diagram
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?
acetyl-CoA + tryptophol
CoA + N-acetyltryptophol
show the reaction diagram
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structural analogue to tryptamine
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?
acetyl-CoA + tyramine
CoA + N-acetyltyramine
show the reaction diagram
-
10% of the activity with 2-phenylethylamine
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?
additional information
?
-
NATURAL SUBSTRATE
NATURAL PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
acetyl-CoA + serotonin
CoA + N-acetylserotonin
show the reaction diagram
METALS and IONS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
additional information
-
activation by salts as a function of ionic strength
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
acetyl-CoA-tryptamine
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IC50: 0.00062 mM, GST-AANAT fusion protein
alpha-trifluoromethyltryptamine
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modest, competitive
bromoacetyltryptamine
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IC50: 0.00128 mM, GST-AANAT fusion protein
CoA-S-N-acetyl-7-hydroxynaphthylethylamine
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fluorescent variant of CoA-T, a bisubstrate inhibitor, synthesis and enzyme binding structure, molecular modelling, overview
desulfo-CoA
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dead end inhibitor analog, competitive versus CoA
Disulfides
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in vivo and in vitro, reversible by dithiothreitol
Peptides containing a disulfide bond
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S 20251
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IC50: 0.0013 mM, GST-AANAT fusion protein
S 27244
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IC50: 0.00026 mM, GST-AANAT fusion protein
S 27481
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IC50: 0.0004 mM, GST-AANAT fusion protein
S 28036
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IC50: 0.00073 mM, GST-AANAT fusion protein
tryptamine-coenzyme A
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a bisubstrate inhibitor, enzyme binding structure, molecular modelling, overview
tryptophol
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dead end inhibitor analog, competitive versus tryptamine
Zn2+
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at low concentration
KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.47
2,5-dimethoxyphenylethylamine
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pH 6.8, 37°C
3.46
2-(2,3-dichlorophenyl)-ethylamine
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pH 6.8, 37°C
0.9
2-(2-chlorophenyl)-ethylamine
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pH 6.8, 37°C
1.76
2-(3,4-dihydroxyphenyl)-ethylamine
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pH 6.8, 37°C
1.31
2-(3-chlorophenyl)-ethylamine
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pH 6.8, 37°C
1.65
2-(3-fluorophenyl)-ethylamine
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pH 6.8, 37°C
1.55
2-(4-bromophenyl)-ethylamine
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pH 6.8, 37°C
2.33
2-(4-chlorophenyl)ethylamine
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pH 6.8, 37°C
1.28
2-(4-fluorophenyl)-ethylamine
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pH 6.8, 37°C
1.91
2-(p-fluorophenyl)-ethylamine
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pH 6.8, 37°C
1.405
2-(p-nitrophenyl)-ethylamine
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pH 6.8, 37°C
1.58
2-(p-tolyl)-ethylamine
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pH 6.8, 37°C
1.37
2-fluorophenylethylamine
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pH 6.8, 37°C
0.49
2-methoxyphenylethylamine
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pH 6.8, 37°C
1.8
2-Phenylethylamine
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pH 6.8, 37°C
2.07
3-methoxy-2-phenylethylamine
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pH 6.8, 37°C
1.815
3-methoxytyramine
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pH 6.8, 37°C
0.18 - 0.265
acetyl-CoA
0.125 - 0.64
serotonin
0.11 - 4
tryptamine
additional information
additional information
-
Ki VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.0003
CoA-S-N-acetyl-7-hydroxynaphthylethylamine
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-
0.00015
tryptamine-CoA
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IC50 VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.00062
acetyl-CoA-tryptamine
Ovis aries
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IC50: 0.00062 mM, GST-AANAT fusion protein
0.00128
bromoacetyltryptamine
Ovis aries
-
IC50: 0.00128 mM, GST-AANAT fusion protein
0.0013
S 20251
Ovis aries
-
IC50: 0.0013 mM, GST-AANAT fusion protein
0.00026
S 27244
Ovis aries
-
IC50: 0.00026 mM, GST-AANAT fusion protein
0.0004
S 27481
Ovis aries
-
IC50: 0.0004 mM, GST-AANAT fusion protein
0.00073
S 28036
Ovis aries
-
IC50: 0.00073 mM, GST-AANAT fusion protein
SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
0.000195
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7.17
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-
additional information
-
enzyme activities of recombinant wild-type and mutant enzymes, overview
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
6.8
-
assay at
TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
37
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assay at
ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
-
SwissProt
Manually annotated by BRENDA team
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE
-
mainly pars tuberalis, much less than in pineal gland, probably different regulation
Manually annotated by BRENDA team
UNIPROT
ENTRY NAME
ORGANISM
NO. OF AA
NO. OF TRANSM. HELICES
MOLECULAR WEIGHT[Da]
SOURCE
Sequence
SNAT_SHEEP
207
0
23077
Swiss-Prot
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
additional information
-
multiple forms, from 10000 Da via 39000 Da to 100000 Da
POSTTRANSLATIONAL MODIFICATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
phosphoprotein
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cAMP-dependent protein kinase-mediated phosphorylation of AANAT T31. Phosphorylation of T31 promotes binding of AANA to the dimeric 14-3-3 protein, which activates AANAT by increasing arylalkylamine affinity. A second AANAT cAMP-dependent protein kinase phosphorylation site, S205, is found to be 55% phosphorylated at night, when T31 is about 40% phosphorylated. AANAT is dual-phosphorylated. Light-exposure at night decreases T31 and S205 phosphorylation
PROTEIN VARIANTS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
H120Q
-
crystallographic studies, role in enzymic reaction
H122Q
-
crystallographic studies, role in enzymic reaction
H122Q/H120Q
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crystallographic studies, role in enzymic reaction
I57A/V59A
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site-directed mutagenesis, the mutant shows reduced enzyme activity and altered inhibitor binding compared to the wild-type enzyme
P64A
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site-directed mutagenesis, the mutant shows reduced enzyme activity and altered inhibitor binding compared to the wild-type enzyme
P64G
-
site-directed mutagenesis, the mutant shows reduced enzyme activity and altered inhibitor binding compared to the wild-type enzyme
P64W
-
site-directed mutagenesis, the mutant shows reduced enzyme activity and altered inhibitor binding compared to the wild-type enzyme
S205A
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1.6fold increase in Km-value for tryptamine compared to wild-type enzyme
T31A
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1.7fold increase in KM-value for tryptamine compared to wild-type enzyme
Y168F
-
crystallographic studies, role in enzymic reaction
additional information
GENERAL STABILITY
ORGANISM
UNIPROT
LITERATURE
acetyl-CoA stabilizes
-
ATP stabilizes
-
freezing markedly decreases activity
-
polyanions stabilize
-
STORAGE STABILITY
ORGANISM
UNIPROT
LITERATURE
0-2°C, up to 72 h
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4°C, 25% loss of activity within 48 h
-
PURIFICATION/commentary
ORGANISM
UNIPROT
LITERATURE
affinity chromatography on Sepharose CoA
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CLONED/commentary
ORGANISM
UNIPROT
LITERATURE
expression of AANAT-(2–207) and mutant enzymes in Escherichia coli strain BL21(DE3)
-
REF.
AUTHORS
TITLE
JOURNAL
VOL.
PAGES
YEAR
ORGANISM (UNIPROT)
PUBMED ID
SOURCE
Namboodiri, M.A.A.; Dubbels, R.; Klein, D.C.
Arylalkylamine N-acetyltransferase from mammalian pineal gland
Methods Enzymol.
142
583-590
1987
Ovis aries, Rattus norvegicus
Manually annotated by BRENDA team
Voisin, P.; Namboodiri, M.A.A.; Klein, D.C.
Arylamine N-acetyltransferase and arylalkylamine N-acetyltransferase in the mammalian pineal gland
J. Biol. Chem.
259
10913-10918
1984
Ovis aries, Rattus norvegicus
Manually annotated by BRENDA team
Namboodiri, M.A.A.; Brownstein, M.J.; Voisin, P.; Weller, J.L.; Klein, D.C.
A simple and rapid method for the purification of ovine pineal arylalkylamine N-acetyltransferase
J. Neurochem.
48
580-585
1987
Ovis aries, Rattus norvegicus
Manually annotated by BRENDA team
Fleming, J.V.; Barrett, P.; Coon, S.L.; Klein, D.C.; Morgan, P.J.
Ovine arylalkylamine N-acetyltransferase in the pineal and pituitary glands: differences in function and regulation
Endocrinology
140
972-978
1999
Ovis aries
Manually annotated by BRENDA team
Obsil, T.; Ghirlando, R.; Klein, D.C.; Ganguly, S.; Dyda, F.
Crystal structure of the 14-3-3zeta:serotonin N-acetyltransferase complex: a role for scaffolding in enzyme regulation
Cell
105
257-267
2001
Ovis aries
Manually annotated by BRENDA team
De Angelis, J.; Gastel, J.; Klein, D.C.; Cole, P.A.
Kinetic analysis of the catalytic mechanism of serotonin N-acetyltransferase (EC 2.3.1.87)
J. Biol. Chem.
273
3045-3050
1998
Ovis aries
Manually annotated by BRENDA team
Scheibner, K.A.; De Angelis, J.; Burley, S.K.; Cole, P.A.
Investigation of the roles of catalytic residues in serotonin N-acetyltransferase
J. Biol. Chem.
277
18118-18126
2002
Ovis aries (Q29495)
Manually annotated by BRENDA team
Khalil, E.M.; De Angelis, J.; Cole, P.A.
Indoleamine analogs as probes of the substrate selectivity and catalytic mechanism of serotonin N-acetyltransferase
J. Biol. Chem.
273
30321-30327
1998
Ovis aries
Manually annotated by BRENDA team
Ferry, G.; Loynel, A.; Kucharczyk, N.; Bertin, S.; Rodriguez, M.; Delagrange, P.; Galizzi, J.P.; Jacoby, E.; Volland, J.P.; Lesieur, D.; Renard, P.; Canet, E.; Fauchere, J.L.; Boutin, J.A.
Substrate specificity and inhibition studies of human serotonin N-acetyltransferase
J. Biol. Chem.
275
8794-8805
2000
Homo sapiens, Ovis aries
Manually annotated by BRENDA team
Ganguly, S.; Weller, J.L.; Ho, A.; Chemineau, P.; Malpaux, B.; Klein, D.C.
Melatonin synthesis: 14-3-3-dependent activation and inhibition of arylalkylamine N-acetyltransferase mediated by phosphoserine-205
Proc. Natl. Acad. Sci. USA
102
1222-1227
2005
Ovis aries
Manually annotated by BRENDA team
Ferry, G.; Ubeaud, C.; Dauly, C.; Mozo, J.; Guillard, S.; Berger, S.; Jimenez, S.; Scoul, C.; Leclerc, G.; Yous, S.; Delagrange, P.; Boutin, J.A.
Purification of the recombinant human serotonin N-acetyltransferase (EC 2.3.1.87): further characterization of and comparison with AANAT from other species
Protein Expr. Purif.
38
84-98
2004
Homo sapiens, Homo sapiens (Q16613), Ovis aries, Rattus norvegicus (Q64666)
Manually annotated by BRENDA team
Zheng, W.; Schwarzer, D.; Lebeau, A.; Weller, J.L.; Klein, D.C.; Cole, P.A.
Cellular stability of serotonin N-acetyltransferase conferred by phosphonodifluoromethylene alanine (Pfa) substitution for Ser-205
J. Biol. Chem.
280
10462-10467
2005
Ovis aries (Q29495)
Manually annotated by BRENDA team
Pavlicek, J.; Coon, S.L.; Ganguly, S.; Weller, J.L.; Hassan, S.A.; Sackett, D.L.; Klein, D.C.
Evidence that proline focuses movement of the floppy loop of arylalkylamine N-acetyltransferase (EC 2.3.1.87)
J. Biol. Chem.
283
14552-14558
2008
Ovis aries (Q29495)
Manually annotated by BRENDA team
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