Information on EC 2.3.1.81 - aminoglycoside 3-N-acetyltransferase

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The expected taxonomic range for this enzyme is: Bacteria, Eukaryota

EC NUMBER
COMMENTARY hide
2.3.1.81
-
RECOMMENDED NAME
GeneOntology No.
aminoglycoside 3-N-acetyltransferase
REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
acetyl-CoA + a 2-deoxystreptamine antibiotic = CoA + N3-acetyl-2-deoxystreptamine antibiotic
show the reaction diagram
-
-
-
-
REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
Acyl group transfer
-
-
-
-
SYSTEMATIC NAME
IUBMB Comments
acetyl-CoA:2-deoxystreptamine-antibiotic N3-acetyltransferase
Different from EC 2.3.1.60 gentamicin 3-N-acetyltransferase. A wide range of antibiotics containing the 2-deoxystreptamine ring can act as acceptors, including gentamicin, kanamycin, tobramycin, neomycin and apramycin.
CAS REGISTRY NUMBER
COMMENTARY hide
60120-42-5
-
ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
Arizona sp.
-
-
-
Manually annotated by BRENDA team
Escherichia coli BL21(DE3) pLysS
strain BL21(DE3) pLysS
TrEMBL
Manually annotated by BRENDA team
strain C600 containing R-factor JR88
-
-
Manually annotated by BRENDA team
strain JR88
-
-
Manually annotated by BRENDA team
Escherichia coli R135/C600
strain R135/C600
-
-
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
strain Travers PST
-
-
Manually annotated by BRENDA team
formerly Microbulbifer degradans
-
-
Manually annotated by BRENDA team
serovar Haifa, isolated from feces
-
-
Manually annotated by BRENDA team
strain ATCC 21294
TrEMBL
Manually annotated by BRENDA team
SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
4-bromo-thiophene-2-carbonyl-S-CoA + amikacin
?
show the reaction diagram
-
-
-
-
?
4-bromo-thiophene-2-carbonyl-S-CoA + gentamicin
?
show the reaction diagram
-
-
-
-
?
4-bromo-thiophene-2-carbonyl-S-CoA + neomycin B
?
show the reaction diagram
-
-
-
-
?
4-bromo-thiophene-2-carbonyl-S-CoA + paromomycin
?
show the reaction diagram
-
-
-
-
?
4-bromo-thiophene-2-carbonyl-S-CoA + tobramycin
?
show the reaction diagram
-
-
-
-
?
5-bromo-thiophene-2-carbonyl-S-CoA + kanamycin A
?
show the reaction diagram
-
-
-
-
?
5-bromo-thiophene-2-carbonyl-S-CoA + neomycin B
?
show the reaction diagram
-
-
-
-
?
6-fluoropicolinyl-CoA + neomycin B
?
show the reaction diagram
-
-
-
-
?
acetyl-CoA + amikacin
CoA + N3'-acetyl-amikacin
show the reaction diagram
-
-
-
-
?
acetyl-CoA + amikacin
CoA + N3'-acetylamikacin
show the reaction diagram
acetyl-CoA + aminoglycoside-aminocyclitol
CoA + ?
show the reaction diagram
-
-
-
?
acetyl-CoA + apramycin
CoA + N3'-acetylapramycin
show the reaction diagram
acetyl-CoA + butirosin
CoA + N3'-acetylbutirosin
show the reaction diagram
-
-
-
?
acetyl-CoA + dactimicin
CoA + N4-acetyldactamicin + N4,N6'-diacetyldactimicin
show the reaction diagram
-
the percentage of dactimicin affinity relative to gentamicin C1a is very high (74.6%) only with AAC(3)-I, to the most other enzymes tested, in spite of the bifunctional AAC(6')/APH(2''), dactamicin is stable
-
-
?
acetyl-CoA + dibekacin
CoA + N3'-acetyldibekacin
show the reaction diagram
acetyl-CoA + gentamicin
CoA + N3'-acetyl-gentamicin
show the reaction diagram
-
-
-
-
?
acetyl-CoA + gentamicin
CoA + N3'-acetylgentamicin
show the reaction diagram
acetyl-CoA + gentamicin A
CoA + N3'-acetylgentamicin A
show the reaction diagram
-
acetylation at 6% the rate of gentamicin C1
-
-
?
acetyl-CoA + gentamicin C
CoA + N3'-acetylgentamicin C
show the reaction diagram
-
acetylation at 86% the rate of gentamicin C1
-
-
?
acetyl-CoA + gentamicin C1
CoA + N3'-acetylgentamicin C1
show the reaction diagram
acetyl-CoA + gentamicin C1a
CoA + N3'-acetylgentamicin C1a
show the reaction diagram
acetyl-CoA + gentamicin C2
CoA + N3'-acetylgentamicin C2
show the reaction diagram
-
acetylation at 84% the rate of gentamicin C1
-
-
?
acetyl-CoA + isepamycin
CoA + N3'-acetylisepamycin
show the reaction diagram
wild-type and recombinant enzyme
-
?
acetyl-CoA + kanamycin
CoA + N3'-acetyl kanamycin
show the reaction diagram
-
-
-
?
acetyl-CoA + kanamycin
CoA + N3'-acetylkanamycin
show the reaction diagram
acetyl-CoA + kanamycin A
CoA + N3'-acetyl-kanamycin A
show the reaction diagram
-
-
-
-
?
acetyl-CoA + kanamycin A
CoA + N3'-acetylkanamycin A
show the reaction diagram
acetyl-CoA + kanamycin B
CoA + N3'-acetylkanamycin B
show the reaction diagram
-
-
-
-
?
acetyl-CoA + lividomycin A
CoA + ?
show the reaction diagram
-
-
-
-
?
acetyl-CoA + neomycin
CoA + ?
show the reaction diagram
-
-
-
?
acetyl-CoA + neomycin
CoA + N2'-acetylneomycin
show the reaction diagram
wild-type and recombinant enzyme
-
?
acetyl-CoA + neomycin B
CoA + ?
show the reaction diagram
acetyl-CoA + neomycin B
CoA + N3'-acetylneomycin B
show the reaction diagram
-
-
-
-
?
acetyl-CoA + neomycin B
CoA + N3-acetyl-neomycin B
show the reaction diagram
acetyl-CoA + netilmicin
CoA + N3'-acetylnetilmicin
show the reaction diagram
acetyl-CoA + paromomycin
CoA + N3'-acetyl-paromomycin
show the reaction diagram
acetyl-CoA + paromomycin
CoA + N3'-acetylparomomycin
show the reaction diagram
-
-
-
?
acetyl-CoA + paromomycin
CoA + N3'-acetylparomomycin B
show the reaction diagram
-
not E. coli
-
-
?
acetyl-CoA + ribostamycin
CoA + ?
show the reaction diagram
acetyl-CoA + sisomicin
CoA + N3'-acetyl-sisomicin
show the reaction diagram
-
-
-
-
?
acetyl-CoA + sisomicin
CoA + N3'-acetylsisomicin
show the reaction diagram
acetyl-CoA + sisomycin
CoA + N3'-acetylsisomycin
show the reaction diagram
acetyl-CoA + spectinomycin
CoA + N3'-acetylspectinomycin
show the reaction diagram
wild-type and recombinant enzyme
-
?
acetyl-CoA + streptomycin
CoA + ?
show the reaction diagram
wild-type and recombinant enzyme
-
?
acetyl-CoA + tobramycin
CoA + N3'-acetyl-tobramycin
show the reaction diagram
-
-
-
-
?
acetyl-CoA + tobramycin
CoA + N3'-acetyltobramycin
show the reaction diagram
butyryl-CoA + kanamycin A
CoA + N3'-butyryl-kanamycin A
show the reaction diagram
-
-
-
-
?
butyryl-CoA + ribostamycin
CoA + ?
show the reaction diagram
-
-
-
?
desulfo-CoA + ribostamycin
?
show the reaction diagram
-
-
-
?
glutaryl-CoA + kanamycin A
?
show the reaction diagram
-
-
-
-
?
glycyl-CoA + amikacin
CoA + N3'-glycyl-amikacin
show the reaction diagram
-
-
-
-
?
glycyl-CoA + gentamicin
CoA + N3'-glycyl-gentamicin
show the reaction diagram
-
-
-
-
?
glycyl-CoA + kanamycin A
CoA + N3'-glycyl-kanamycin A
show the reaction diagram
-
-
-
-
?
glycyl-CoA + neomycin B
CoA + N3-glycylneomycin B
show the reaction diagram
-
-
-
-
?
glycyl-CoA + sisomicin
CoA + N3'-glycyl-sisomicin
show the reaction diagram
-
-
-
-
?
malonyl-CoA + amikacin
CoA + N3'-malonyl-amikacin
show the reaction diagram
-
-
-
-
?
malonyl-CoA + gentamicin
CoA + N3'-malonyl-gentamicin
show the reaction diagram
-
-
-
-
?
malonyl-CoA + kanamycin A
CoA + N3'-malonylkanamycin A
show the reaction diagram
-
-
-
-
?
malonyl-CoA + neomycin B
CoA + N3-malonylneomycin B
show the reaction diagram
-
-
-
-
?
malonyl-CoA + ribostamycin
CoA + ?
show the reaction diagram
-
-
-
?
methylmalonyl-CoA + neomycin B
CoA + N3-methylmalonylneomycin B
show the reaction diagram
-
-
-
-
?
N-propionyl-CoA + amikacin
CoA + N3'-propionyl-amikacin
show the reaction diagram
-
-
-
-
?
N-propionyl-CoA + gentamicin
CoA + N3'-propionyl-gentamicin
show the reaction diagram
-
-
-
-
?
n-propionyl-CoA + kanamycin A
CoA + N3'-n-propionylkanamycin A
show the reaction diagram
-
-
-
-
?
N-propionyl-CoA + kanamycin A
CoA + N3'-propionyl-kanamycin A
show the reaction diagram
-
-
-
-
?
N-propionyl-CoA + neomycin B
CoA + N3-propionylneomycin B
show the reaction diagram
-
-
-
-
?
N-propionyl-CoA + paromomycin
CoA + N3'-propionyl-paromomycin
show the reaction diagram
-
-
-
-
?
N-propionyl-CoA + sisomicin
CoA + N3'-propionyl-sisomicin
show the reaction diagram
-
-
-
-
?
N-propionyl-CoA + tobramycin
CoA + N3'-propionyl-tobramycin
show the reaction diagram
-
-
-
-
?
propionyl-CoA + ribostamycin
CoA + ?
show the reaction diagram
-
-
-
?
additional information
?
-
NATURAL SUBSTRATES
NATURAL PRODUCTS
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
additional information
?
-
-
AAC(3)-Id is responsible for the gain of resistance to diverse agents, i.e. gentamicin C1a, gentamicin C1, sisomicin, neomycin, dibekacin, kanamycin, tobramycin, amikacin, netilmicin, apramycin, dactimicin, spectinomycin, streptomycin, lividomycin, and butirosin, in Salmonella enterica serovar Haifa, overview
-
-
-
METALS and IONS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
Ca2+
-
1.0 mM, about 100% activity enhancement
Mg2+
-
1.5 mM, about 100% activity enhancement
NH4+
-
slight activation
INHIBITORS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
3-(dimethylamino)propylamine
-
0.5 mM, 30% residual activity
acetyltobramycin
-
-
amikacin
-
-
Butyryl-CoA
-
dead-end inhibition pattern
CoA
-
product inhibition
EDTA
-
above 0.5 mM
gentamicin C1a
-
substrate inhibition
kanamycin A
-
substrate inhibition
kanamycin B
-
substrate inhibition
N-cyclohexyl-3-(3-dimethylamino-propylamino)-propionamide
-
0.5 mM, 77% inhibition
N-[2-(3,4-dimethoxyphenyl)-ethyl]-3-(3-dimethylamino-propylamino)-propionamide
-
0.5 mM, 63% inhibition
N3-Acetyltobramycin
-
product inhibition
neomycin
-
-
ribostamycin
tobramycin
-
substrate inhibition
additional information
KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.0013 - 0.17
acetyl-CoA
0.00096 - 11.07
amikacin
0.00067
apramycin
in 50 mM HEPES, pH 7.5 and 0.1 mM 4,4'-dithiodipyridine, at pH 7.8 and 25C
0.237
butirosin
in 50 mM HEPES, pH 7.5 and 0.1 mM 4,4'-dithiodipyridine, at pH 7.8 and 25C
1.16
Butyryl-CoA
in 50 mM HEPES, pH 7.5 and 0.1 mM 4,4'-dithiodipyridine, at pH 7.8 and 25C
0.0029 - 0.0189
gentamicin
0.066
gentamicin C1
-
-
0.00012
gentamicin C1a
-
-
0.00097
gentamycin
in 50 mM HEPES, pH 7.5 and 0.1 mM 4,4'-dithiodipyridine, at pH 7.8 and 25C
0.002 - 0.238
kanamycin A
0.0026
kanamycin B
-
pH 7.6, 25C
0.0036
lividomycin A
-
pH 7.6, 25C
0.234 - 0.477
malonyl-CoA
0.0886
n-propionyl-CoA
-
cosubstrate kanamycin A, pH 7.6, 25C
0.00036
neomycin
in 50 mM HEPES, pH 7.5 and 0.1 mM 4,4'-dithiodipyridine, at pH 7.8 and 25C
0.0012 - 0.0148
neomycin B
0.042
netilmicin
in 50 mM HEPES, pH 7.5 and 0.1 mM 4,4'-dithiodipyridine, at pH 7.8 and 25C
0.00015 - 0.0033
paromomycin
0.499
propionyl-CoA
in 50 mM HEPES, pH 7.5 and 0.1 mM 4,4'-dithiodipyridine, at pH 7.8 and 25C
0.0023 - 0.0031
ribostamycin
0.00057 - 0.0015
sisomicin
0.00033 - 0.0015
sisomycin
0.0013 - 0.0054
tobramycin
additional information
additional information
-
kinetic pattern
-
TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
10.5 - 39.4
acetyl-CoA
0.124 - 0.5
amikacin
61
apramycin
Escherichia coli
Q306W4
in 50 mM HEPES, pH 7.5 and 0.1 mM 4,4'-dithiodipyridine, at pH 7.8 and 25C
3.5
butirosin
Escherichia coli
Q306W4
in 50 mM HEPES, pH 7.5 and 0.1 mM 4,4'-dithiodipyridine, at pH 7.8 and 25C
0.3
Butyryl-CoA
Escherichia coli
Q306W4
in 50 mM HEPES, pH 7.5 and 0.1 mM 4,4'-dithiodipyridine, at pH 7.8 and 25C
0.041 - 0.182
gentamicin
40
gentamycin
Escherichia coli
Q306W4
in 50 mM HEPES, pH 7.5 and 0.1 mM 4,4'-dithiodipyridine, at pH 7.8 and 25C
0.012 - 80
kanamycin A
54.5
kanamycin B
Pseudomonas aeruginosa
-
pH 7.6, 25C
33.8
lividomycin A
Pseudomonas aeruginosa
-
pH 7.6, 25C
5.7 - 9
malonyl-CoA
10.2
n-propionyl-CoA
Pseudomonas aeruginosa
-
cosubstrate kanamycin A, pH 7.6, 25C
60
neomycin
Escherichia coli
Q306W4
in 50 mM HEPES, pH 7.5 and 0.1 mM 4,4'-dithiodipyridine, at pH 7.8 and 25C
0.076 - 9.5
neomycin B
32
netilmicin
Escherichia coli
Q306W4
in 50 mM HEPES, pH 7.5 and 0.1 mM 4,4'-dithiodipyridine, at pH 7.8 and 25C
15 - 33.6
paromomycin
33
propionyl-CoA
Escherichia coli
Q306W4
in 50 mM HEPES, pH 7.5 and 0.1 mM 4,4'-dithiodipyridine, at pH 7.8 and 25C
23.5 - 146
ribostamycin
0.121 - 0.173
sisomicin
46.3 - 51
sisomycin
0.089 - 162
tobramycin
kcat/KM VALUE [1/mMs-1]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
600 - 2600
acetyl-CoA
11200
kanamycin A
Pseudomonas aeruginosa
-
pH 7.6, 25C
789
34400
kanamycin B
Pseudomonas aeruginosa
-
pH 7.6, 25C
3078
9500
lividomycin A
Pseudomonas aeruginosa
-
pH 7.6, 25C
11575
30
malonyl-CoA
Pseudomonas aeruginosa
-
cosubstrate kanamycin A, pH 7.6, 25C
76
120
n-propionyl-CoA
Pseudomonas aeruginosa
-
cosubstrate kanamycin A, pH 7.6, 25C
3481
9100
neomycin B
Pseudomonas aeruginosa
-
pH 7.6, 25C
2279
10800
paromomycin
Pseudomonas aeruginosa
-
pH 7.6, 25C
2215
10600
ribostamycin
Pseudomonas aeruginosa
-
pH 7.6, 25C
1627
33400
sisomycin
Pseudomonas aeruginosa
-
pH 7.6, 25C
7522
60500
tobramycin
Pseudomonas aeruginosa
-
pH 7.6, 25C
939
Ki VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.381
kanamycin A
-
pH 7.6, 25C
0.0059
ribostamycin
-
pH 7.6, 25C
SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
9.743
-
pH 7.2, 34C
additional information
-
Vmax 0.102 (sisomicin), pH 7.2, 34C
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
6.6
-
assay at
8
corresponds to the plateau region of the pH profile, where the velocity is maximal and the variations in velocity due to changes in pH are smallest
TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
25
-
assay at
pI VALUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
5.7
calculated from amino acid sequence
LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY hide
GeneOntology No.
LITERATURE
SOURCE
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
18630
-
18649 Da predicted from nucleotide sequence, 18630 Da found by mass spectrometry
54000
dynamic light scattering
55750
calculated from amino acid sequence
60000
Sephacryl-S200 gel filtration
additional information
-
amino acid analysis
SUBUNITS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
POSTTRANSLATIONAL MODIFICATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
side-chain modification
-
cleavage of the hexahistidine tag by tobacco etch virus protease
Crystallization/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
X-ray structure of a recombinant enzyme, expressed in its selenomethionine substituted form, cocrystallization with 5 mM CoA at 4C and pH: 7.8, crystal cryoprotection achieved with 17% glycerol and 8% 2R,3R-butanediol, active center found by X-ray analysis and model building
-
TEMPERATURE STABILITY
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
40
-
above, inactivation within 2 min
GENERAL STABILITY
ORGANISM
UNIPROT
LITERATURE
dialysis against EDTA with subsequent Mg2+-addition to dialyzed enzyme has no effect on activity
-
enzyme activity is significantly stabilized when preparations contain substrate
-
gel filtration leads to complete inactivation
-
STORAGE STABILITY
ORGANISM
UNIPROT
LITERATURE
-20C, partially purified, several months
-
-20C, purified, several days
-
Purification/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
Fast Flow Q-Sepharose anion exchange column chromatography and Phenyl Sepharose column chromatography
Ni2+-affinity chromatography
plasmid pPK237 transferred to and expressed in E. coli K12, affinity chromatography
-
Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
expressed in Escherichia coli
expressed in the pET-23a(+) expression vector
expression in Escherichia coli
-
expression in Escherichia coli DH5alpha
expression in Escherichia coli K802N by mating
expression of C- or N-terminally His-tagged enzyme from vectors pET22b, and pET28a or Int-pET19b-pps, respectively
-
gene aac(3)-Id, in a class 1 integron
-
plasmid transfer pIJ702 to Streptomyces lividans TK21
-
Pseudomonas aeruginosa plasmid pPK237 transferred to and expressed in Escherichia coli K12
-
wild-type and truncated enzymes expressed in Escherichia coli
-
APPLICATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
medicine
synthesis
-
development of a methodology that utilizes aminoglycoside acetyltransferase and unnatural acyl-CoA analogues for the chemoenzymatic generation of regioselectively N-acylatedaminoglycoside analogues. Aminoglycosides are broad-spectrum antibiotics commonly used for the treatment of serious bacterial infections
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