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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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Ovis aries
UNIPROT: Q29495
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The taxonomic range for the selected organisms is: Ovis aries
The expected taxonomic range for this enzyme is: Eukaryota, Bacteria
Synonyms
aanat, aa-nat, snat2, arylalkylamine n-acetyltransferase, snat1, aanat2, aanat1, serotonin-n-acetyltransferase, aralkylamine n-acetyltransferase, bm-iaanat, more
SYNONYM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
AA-NAT
-
-
-
-
AANAT
acetyl-CoA:aralkylamine N-acetyltransferase
-
-
-
-
acetyltransferase, arylalkylamine N-
-
-
-
-
arylalkylamine N-acetyltransferase
-
-
-
-
N-acetyltransferase
-
-
-
-
oAANAT
-
-
serotonin acetylase
-
-
-
-
serotonin acetyltransferase
-
-
-
-
additional information
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
-
-
-
-
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 + serotonin
CoA + N-acetylserotonin
show the reaction diagram
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
-
60% of the activity with 2-phenylethylamine
-
-
?
acetyl-CoA + 2-(p-fluorophenyl)-ethylamine
CoA + N-acetyl-2-(p-fluorophenyl)-ethylamine
show the reaction diagram
-
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
-
-
?
acetyl-CoA + 3-indolepropylamine
CoA + N-acetyl-(3-indol-3-yl-propyl)-amine
show the reaction diagram
-
20-fold less efficiently than serotonin
-
-
?
acetyl-CoA + 3-methoxy-2-phenylethylamine
CoA + N-acetyl-3-methoxy-2-phenylethylamine
show the reaction diagram
-
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
-
1% of the activity with 2-phenylethylamine
-
-
?
acetyl-CoA + 4-(2-aminoethyl)-benzenesulfonyl fluoride
CoA + ?
show the reaction diagram
-
7.4% of the activity with 2-phenylethylamine
-
-
?
acetyl-CoA + 4-methoxyphenylethylamine
CoA + N-acetyl-4-methoxyphenylethylamine
show the reaction diagram
-
10% of the activity with 2-phenylethylamine
-
-
?
acetyl-CoA + 5-hydroxydopamine
CoA + N-acetyl-5-hydroxydopamine
show the reaction diagram
-
4.4% of the activity with 2-phenylethylamine
-
-
?
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
-
-
?
acetyl-CoA + alpha-methyltryptamine
CoA + N-acetyl-alpha-methyltryptamine
show the reaction diagram
-
racemic, 9:1 stereoselectivity for R-enantiomer, less efficiently than serotonin
-
-
?
acetyl-CoA + beta-phenylethylamine
CoA + N-(2-phenylethyl)-acetaminde
show the reaction diagram
-
-
-
-
?
acetyl-CoA + Nomega-methyltryptamine
CoA + ?
show the reaction diagram
-
less efficiently than serotonin
-
-
?
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
-
-
-
-
?
acetyl-CoA + tryptophol
CoA + N-acetyltryptophol
show the reaction diagram
-
structural analogue to tryptamine
-
-
?
acetyl-CoA + tyramine
CoA + N-acetyltyramine
show the reaction diagram
-
10% of the activity with 2-phenylethylamine
-
-
?
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
penultimate step in melatonin biosynthesis
-
-
?
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
CoA-S-N-acetyl-7-hydroxynaphthylethylamine
fluorescent variant of CoA-T, a bisubstrate inhibitor, synthesis and enzyme binding structure, molecular modelling, overview
morin
0.1 mM, 2fold inhibition
myricetin
0.1 mM, 1.6fold inhibition
quercetin
0.1 mM, 1.2fold inhibition
tryptamine-coenzyme A
a bisubstrate inhibitor, enzyme binding structure, molecular modelling, overview
acetyl-CoA-tryptamine
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IC50: 0.00062 mM, GST-AANAT fusion protein
alpha-trifluoromethyltryptamine
-
modest, competitive
bromoacetyltryptamine
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IC50: 0.00128 mM, GST-AANAT fusion protein
desulfo-CoA
-
dead end inhibitor analog, competitive versus CoA
Disulfides
-
in vivo and in vitro, reversible by dithiothreitol
Peptides containing a disulfide bond
-
-
-
S 20251
-
IC50: 0.0013 mM, GST-AANAT fusion protein
S 27244
-
IC50: 0.00026 mM, GST-AANAT fusion protein
S 27481
-
IC50: 0.0004 mM, GST-AANAT fusion protein
S 28036
-
IC50: 0.00073 mM, GST-AANAT fusion protein
tryptophol
-
dead end inhibitor analog, competitive versus tryptamine
Zn2+
-
at low concentration
KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.33 - 4
tryptamine
0.47
2,5-dimethoxyphenylethylamine
-
pH 6.8, 37°C
3.46
2-(2,3-dichlorophenyl)-ethylamine
-
pH 6.8, 37°C
0.9
2-(2-chlorophenyl)-ethylamine
-
pH 6.8, 37°C
1.76
2-(3,4-dihydroxyphenyl)-ethylamine
-
pH 6.8, 37°C
1.31
2-(3-chlorophenyl)-ethylamine
-
pH 6.8, 37°C
1.65
2-(3-fluorophenyl)-ethylamine
-
pH 6.8, 37°C
1.55
2-(4-bromophenyl)-ethylamine
-
pH 6.8, 37°C
2.33
2-(4-chlorophenyl)ethylamine
-
pH 6.8, 37°C
1.28
2-(4-fluorophenyl)-ethylamine
-
pH 6.8, 37°C
1.91
2-(p-fluorophenyl)-ethylamine
-
pH 6.8, 37°C
1.405
2-(p-nitrophenyl)-ethylamine
-
pH 6.8, 37°C
1.58
2-(p-tolyl)-ethylamine
-
pH 6.8, 37°C
1.37
2-fluorophenylethylamine
-
pH 6.8, 37°C
0.49
2-methoxyphenylethylamine
-
pH 6.8, 37°C
1.8
2-Phenylethylamine
-
pH 6.8, 37°C
2.07
3-methoxy-2-phenylethylamine
-
pH 6.8, 37°C
1.815
3-methoxytyramine
-
pH 6.8, 37°C
0.18 - 0.265
acetyl-CoA
0.125 - 0.64
serotonin
0.11 - 0.31
tryptamine
additional information
additional information
-
Ki VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.0003
CoA-S-N-acetyl-7-hydroxynaphthylethylamine
-
0.00015
tryptamine-CoA
-
IC50 VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.00062
acetyl-CoA-tryptamine
Ovis aries
-
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
-
-
7.17
-
-
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
assay at
ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
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
LOCALIZATION PREDICTION?
SNAT_SHEEP
207
0
23077
Swiss-Prot
Mitochondrion (Reliability: 5)
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
-
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
crystallographic studies, role in enzymic reaction
I57A/V59A
site-directed mutagenesis, the mutant shows reduced enzyme activity and altered inhibitor binding compared to the wild-type enzyme
P64A
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
Y168F
crystallographic studies, role in enzymic reaction
S205A
-
1.6fold increase in Km-value for tryptamine compared to wild-type enzyme
T31A
-
1.7fold increase in KM-value for tryptamine compared to wild-type enzyme
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
-
4°C, 25% loss of activity within 48 h
-
PURIFICATION (Commentary)
ORGANISM
UNIPROT
LITERATURE
affinity chromatography on Sepharose CoA
-
CLONED (Commentary)
ORGANISM
UNIPROT
LITERATURE
expression of AANAT-(2–207) and mutant enzymes in Escherichia coli strain BL21(DE3)
APPLICATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
synthesis
recombinant Escherichia coli that expresses sheep SNAT with rice caffeic acid O-methyltransferase produces up to 1.46 mg/l meatonin in culture medium in response to 1 mM serotonin
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
Ovis aries, Homo sapiens
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
Ovis aries, Homo sapiens (Q16613), Homo sapiens, 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
Byeon, Y.; Back, K.
Melatonin production in Escherichia coli by dual expression of serotonin N-acetyltransferase and caffeic acid O-methyltransferase
Appl. Microbiol. Biotechnol.
100
6683-6691
2016
Ovis aries (Q29495)
Manually annotated by BRENDA team
Lee, K.; Hwang, O.J.; Reiter, R.J.; Back, K.
Flavonoids inhibit both rice and sheep serotonin N-acetyltransferases and reduce melatonin levels in plants
J. Pineal Res.
65
e12512
2018
Oryza sativa, Ovis aries (Q29495), Ovis aries
Manually annotated by BRENDA team