Information on EC 2.3.1.81 - aminoglycoside N3'-acetyltransferase

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

EC NUMBER
COMMENTARY
2.3.1.81
-
RECOMMENDED NAME
GeneOntology No.
aminoglycoside N3'-acetyltransferase
REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT ACCESSION NO.
LITERATURE
acetyl-CoA + a 2-deoxystreptamine antibiotic = CoA + N3'-acetyl-2-deoxystreptamine antibiotic
show the reaction diagram
-
-
-
-
REACTION TYPE
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
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.
SYNONYMS
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
3'-aminoglycoside acetyltransferase
-
-
-
-
3-N-acetyltransferase
-
-
-
3-N-aminoglycoside acetyltransferase
-
-
-
3-N-aminoglycoside acetyltransferase
Q65741
-
AAC (3)-IIIb
-
-
AAC(3)
-
-
AAC(3)-Id
-
-
AAC(3)-Ig acetyltransferase
-
-
AAC(3)-IV
-
-
AAC(3)-IV
Q306W4
-
AAC(3)-IV
Escherichia coli BL21(DE3) pLysS
Q306W4
-
-
AAC(6')-APH(2'')
-
-
AAC3-IV aminoglycoside acetyltransferase
Q306W4
-
AAC3-IV aminoglycoside acetyltransferase
Escherichia coli BL21(DE3) pLysS
Q306W4
-
-
AacC-A7 acetyltransferase
-
-
aminoglycoside 3-acetyltransferase
-
-
aminoglycoside 3-acetyltransferase-IIIb
-
-
aminoglycoside 3-N-acetyltransferase
Q306W4
-
aminoglycoside 3-N-acetyltransferase
Escherichia coli BL21(DE3) pLysS
Q306W4
-
-
aminoglycoside 3-N-acetyltransferase
-
-
aminoglycoside 3-N-acetyltransferase
-
-
aminoglycoside 3-N-acetyltransferase
Q54216
-
aminoglycoside 3-N-acetyltransferase
Q4R0X5
-
aminoglycoside acetyltransferase
-
-
aminoglycoside acetytransferase
-
-
additional information
-
-
-
CAS REGISTRY NUMBER
COMMENTARY
60120-42-5
-
ORGANISM
COMMENTARY
LITERATURE
SEQUENCE CODE
SEQUENCE DB
SOURCE
Arizona sp.
-
-
-
Manually annotated by BRENDA team
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
strain R135/C600
-
-
Manually annotated by BRENDA team
strains K802N, W677, p75-24, S3035, JR225, JR226, JR227
-
-
Manually annotated by BRENDA team
Escherichia coli BL21(DE3) pLysS
strain BL21(DE3) pLysS
TrEMBL
Manually annotated by BRENDA team
Escherichia coli C600
strain C600 containing R-factor JR88
-
-
Manually annotated by BRENDA team
Escherichia coli JR88
strain JR88
-
-
Manually annotated by BRENDA team
Escherichia coli R135/C600
strain R135/C600
-
-
Manually annotated by BRENDA team
phenotype of VA-182/00
SwissProt
Manually annotated by BRENDA team
plasmid pPK237 transferred to and expressed in Escherichia coli K12
-
-
Manually annotated by BRENDA team
strain Travers PST
-
-
Manually annotated by BRENDA team
Pseudomonas aeruginosa Travers
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
SS-1198 and SS-1198PR mutant
-
-
Manually annotated by BRENDA team
strain ATCC 21294
TrEMBL
Manually annotated by BRENDA team
SUBSTRATE
PRODUCT                      
REACTION DIAGRAM
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
(Substrate)
LITERATURE
(Substrate)
COMMENTARY
(Product)
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'-acetylamikacin
show the reaction diagram
-, Q306W4
-
-
-
?
acetyl-CoA + amikacin
CoA + N3'-acetylamikacin
show the reaction diagram
-, Q83V16
wild-type and recombinant enzyme
-
?
acetyl-CoA + amikacin
CoA + N3'-acetylamikacin
show the reaction diagram
Escherichia coli BL21(DE3) pLysS
Q306W4
-
-
-
?
acetyl-CoA + amikacin
CoA + N3'-acetyl-amikacin
show the reaction diagram
-
-
-
-
?
acetyl-CoA + aminoglycoside-aminocyclitol
CoA + ?
show the reaction diagram
Q4R0X5, -
-
-
-
?
acetyl-CoA + apramycin
CoA + N3'-acetylapramycin
show the reaction diagram
-, Q306W4
-
-
-
?
acetyl-CoA + apramycin
CoA + N3'-acetylapramycin
show the reaction diagram
-
a wide range of antibiotics containing the 2-deoxystreptamine ring can act as acceptors, including gentamicin, kanamycin, tobramycin, neomycin
-
?
acetyl-CoA + apramycin
CoA + N3'-acetylapramycin
show the reaction diagram
Escherichia coli BL21(DE3) pLysS
Q306W4
-
-
-
?
acetyl-CoA + butirosin
CoA + N3'-acetylbutirosin
show the reaction diagram
-, Q306W4
-
-
-
?
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 + dibekacin
CoA + N3'-acetyldibekacin
show the reaction diagram
-
acetylation at 8% the rate of gentamicin C1
-
-
?
acetyl-CoA + dibekacin
CoA + N3'-acetyldibekacin
show the reaction diagram
Escherichia coli JR88
-
-
-
-
?
acetyl-CoA + gentamicin
CoA + N3'-acetylgentamicin
show the reaction diagram
-
-
-
?
acetyl-CoA + gentamicin
CoA + N3'-acetylgentamicin
show the reaction diagram
-, Q306W4
-
-
-
?
acetyl-CoA + gentamicin
CoA + N3'-acetylgentamicin
show the reaction diagram
-, Q83V16
wild-type and recombinant enzyme
-
?
acetyl-CoA + gentamicin
CoA + N3'-acetylgentamicin
show the reaction diagram
Escherichia coli BL21(DE3) pLysS
Q306W4
-
-
-
?
acetyl-CoA + gentamicin
CoA + N3'-acetyl-gentamicin
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 C1
CoA + N3'-acetylgentamicin C1
show the reaction diagram
-
best substrate
-
-
?
acetyl-CoA + gentamicin C1
CoA + N3'-acetylgentamicin C1
show the reaction diagram
Pseudomonas aeruginosa Travers, Escherichia coli R135/C600
-
-
-
-
?
acetyl-CoA + gentamicin C1a
CoA + N3'-acetylgentamicin C1a
show the reaction diagram
-
-
-
?
acetyl-CoA + gentamicin C1a
CoA + N3'-acetylgentamicin C1a
show the reaction diagram
-
-
-
-
?
acetyl-CoA + gentamicin C1a
CoA + N3'-acetylgentamicin C1a
show the reaction diagram
-
acetylation at 60% the rate of gentamicin C1
-
?
acetyl-CoA + gentamicin C1a
CoA + N3'-acetylgentamicin C1a
show the reaction diagram
Escherichia coli JR88
-
-
-
-
?
acetyl-CoA + gentamicin C1a
CoA + N3'-acetylgentamicin C1a
show the reaction diagram
Escherichia coli C600
-
-
-
?
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
-, Q83V16
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
-, Q306W4
-
-
-
?
acetyl-CoA + kanamycin
CoA + N3'-acetylkanamycin
show the reaction diagram
-, Q83V16
wild-type and recombinant enzyme
-
-
acetyl-CoA + kanamycin
CoA + N3'-acetylkanamycin
show the reaction diagram
Escherichia coli BL21(DE3) pLysS
Q306W4
-
-
-
?
acetyl-CoA + kanamycin A
CoA + N3'-acetylkanamycin A
show the reaction diagram
-
-
-
-
?
acetyl-CoA + kanamycin A
CoA + N3'-acetylkanamycin A
show the reaction diagram
-
-
-
-
?
acetyl-CoA + kanamycin A
CoA + N3'-acetylkanamycin A
show the reaction diagram
-
acetylation at 7% the rate of gentamicin C1
-
-
?
acetyl-CoA + kanamycin A
CoA + N3'-acetylkanamycin A
show the reaction diagram
Pseudomonas aeruginosa Travers, Escherichia coli R135/C600
-
-
-
-
?
acetyl-CoA + kanamycin A
CoA + N3'-acetyl-kanamycin 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 + N2'-acetylneomycin
show the reaction diagram
-, Q83V16
wild-type and recombinant enzyme
-
?
acetyl-CoA + neomycin
CoA + ?
show the reaction diagram
-, Q306W4
-
-
-
?
acetyl-CoA + neomycin B
CoA + ?
show the reaction diagram
-
-
-
-
?
acetyl-CoA + neomycin B
CoA + ?
show the reaction diagram
Escherichia coli JR88
-
-
-
-
?
acetyl-CoA + neomycin B
CoA + N3-acetyl-neomycin B
show the reaction diagram
-
-
-
-
?
acetyl-CoA + neomycin B
CoA + N3-acetyl-neomycin B
show the reaction diagram
-
-
-
-
?
acetyl-CoA + neomycin B
CoA + N3'-acetylneomycin B
show the reaction diagram
-
-
-
-
?
acetyl-CoA + netilmicin
CoA + N3'-acetylnetilmicin
show the reaction diagram
-, Q306W4
-
-
-
?
acetyl-CoA + netilmicin
CoA + N3'-acetylnetilmicin
show the reaction diagram
-, Q83V16
wild-type and recombinant enzyme
-
?
acetyl-CoA + netilmicin
CoA + N3'-acetylnetilmicin
show the reaction diagram
Escherichia coli, Escherichia coli JR88
-
the much higher treshold value for the modification of netilmicin as compared with the one for the modification of sisomicin is due to the 1-N side chain
-
-
?
acetyl-CoA + paromomycin
CoA + N3'-acetylparomomycin B
show the reaction diagram
-
not E. coli
-
-
?
acetyl-CoA + paromomycin
CoA + N3'-acetylparomomycin
show the reaction diagram
-, Q306W4
-
-
-
?
acetyl-CoA + paromomycin
CoA + N3'-acetyl-paromomycin
show the reaction diagram
-
-
-
-
?
acetyl-CoA + paromomycin
CoA + N3'-acetyl-paromomycin
show the reaction diagram
-
-
-
-
?
acetyl-CoA + ribostamycin
CoA + ?
show the reaction diagram
-
-
-
-
?
acetyl-CoA + ribostamycin
CoA + ?
show the reaction diagram
-, Q306W4
-
-
-
?
acetyl-CoA + sisomicin
CoA + N3'-acetylsisomicin
show the reaction diagram
-
-
-
-
?
acetyl-CoA + sisomicin
CoA + N3'-acetylsisomicin
show the reaction diagram
-
-
-
-
-
acetyl-CoA + sisomicin
CoA + N3'-acetylsisomicin
show the reaction diagram
-
best substrate
-
?
acetyl-CoA + sisomicin
CoA + N3'-acetylsisomicin
show the reaction diagram
-
best substrate
-
-
?
acetyl-CoA + sisomicin
CoA + N3'-acetylsisomicin
show the reaction diagram
-
best substrate
-
?
acetyl-CoA + sisomicin
CoA + N3'-acetylsisomicin
show the reaction diagram
-, Q83V16
wild-type and recombinant enzyme
-
?
acetyl-CoA + sisomicin
CoA + N3'-acetylsisomicin
show the reaction diagram
-
acetylation at 51% the rate of gentamicin C1
-
-
?
acetyl-CoA + sisomicin
CoA + N3'-acetylsisomicin
show the reaction diagram
Escherichia coli JR88
-
best substrate
-
-
?
acetyl-CoA + sisomicin
CoA + N3'-acetylsisomicin
show the reaction diagram
Pseudomonas aeruginosa Travers
-
best substrate
-
?
acetyl-CoA + sisomicin
CoA + N3'-acetylsisomicin
show the reaction diagram
Escherichia coli C600
-
-
-
-
?
acetyl-CoA + sisomicin
CoA + N3'-acetylsisomicin
show the reaction diagram
Escherichia coli R135/C600
-
best substrate
-
?
acetyl-CoA + sisomicin
CoA + N3'-acetyl-sisomicin
show the reaction diagram
-
-
-
-
?
acetyl-CoA + sisomycin
CoA + N3'-acetylsisomycin
show the reaction diagram
-
-
-
-
?
acetyl-CoA + sisomycin
CoA + N3'-acetylsisomycin
show the reaction diagram
-, Q306W4
-
-
-
?
acetyl-CoA + spectinomycin
CoA + N3'-acetylspectinomycin
show the reaction diagram
-, Q83V16
wild-type and recombinant enzyme
-
?
acetyl-CoA + streptomycin
CoA + ?
show the reaction diagram
-, Q83V16
wild-type and recombinant enzyme
-
?
acetyl-CoA + tobramycin
CoA + N3'-acetyltobramycin
show the reaction diagram
-
-
-
-
?
acetyl-CoA + tobramycin
CoA + N3'-acetyltobramycin
show the reaction diagram
-
-
-
-
?
acetyl-CoA + tobramycin
CoA + N3'-acetyltobramycin
show the reaction diagram
-, Q306W4
-
-
-
?
acetyl-CoA + tobramycin
CoA + N3'-acetyltobramycin
show the reaction diagram
-, Q83V16
wild-type and recombinant enzyme
-
?
acetyl-CoA + tobramycin
CoA + N3'-acetyltobramycin
show the reaction diagram
-
acetylation at 6% the rate of gentamicin C1
-
-
?
acetyl-CoA + tobramycin
CoA + N3'-acetyltobramycin
show the reaction diagram
Pseudomonas aeruginosa Travers
-
-
-
-
?
acetyl-CoA + tobramycin
CoA + N3'-acetyltobramycin
show the reaction diagram
Escherichia coli C600
-
-
-
-
?
acetyl-CoA + tobramycin
CoA + N3'-acetyltobramycin
show the reaction diagram
Escherichia coli BL21(DE3) pLysS
Q306W4
-
-
-
?
acetyl-CoA + tobramycin
CoA + N3'-acetyltobramycin
show the reaction diagram
Escherichia coli R135/C600
-
-
-
-
?
acetyl-CoA + tobramycin
CoA + N3'-acetyl-tobramycin
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
-, Q306W4
-
-
-
?
desulfo-CoA + ribostamycin
?
show the reaction diagram
-, Q306W4
-
-
-
?
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
-, Q306W4
-
-
-
?
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'-propionyl-kanamycin A
show the reaction diagram
-
-
-
-
?
n-propionyl-CoA + kanamycin A
CoA + N3'-n-propionylkanamycin 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
-, Q306W4
-
-
-
?
methylmalonyl-CoA + neomycin B
CoA + N3-methylmalonylneomycin B
show the reaction diagram
-
-
-
-
?
additional information
?
-
-
no substrates are amikacin
-
-
-
additional information
?
-
-
no substrates are amikacin, lividomycin A, butirosin A and B
-
-
-
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
-
-
-
additional information
?
-
-
no activity with benzoyl-CoA, acetoacetyl-CoA, crotonyl-CoA, isovaleryl-CoA, palmitoyl-CoA, and DL-3-hydroxy-butyryl-CoA by AAC(6')-APH(2'')
-
-
-
additional information
?
-
-
CoASH associates with a high-affinity, catalytic site and with a secondary, low-affinity site that overlaps with the antibiotic binding pocket. The binding of CoASH to the high-affinity site occurs with a small, unfavorable enthalpy and a favorable entropy. Binding to the second site is highly exothermic and is accompanied by an unfavorable entropic contribution. The presence of an aminoglycoside alters the binding of CoASH to the enzyme dramatically such that the binding occurs with a favorable enthalpy and an unfavorable entropy. This is irrespective of which aminoglycoside is the cosubstrate and occurs without a significant change in the affinity of CoASH for the enzyme. The presence of antibiotics eliminates binding of CoASH to the second site
-
-
-
additional information
?
-
-
enzyme displays molecular size-dependent stoichiometry where binding stoichiometries are 1.5-2.0 for small antibiotics and 1.0 for larger. Antibiotic-enzyme interaction occurs with a favorable enthalpy and a compensating unfavorable entropy. The presence of coenzyme A significantly increases the affinity of the antibioticthe enthalpy of binding becomes more favored by 1.7-10.0fold in the presence of the cosubstrate CoASH, while the entropy becomes 2.0-22.5fold less favored. The overall free energy change is still only 1.0-1.9 kcal/mol from binary to ternary for all antibiotics tested, similar to those for other aminoglycoside-modifying enzymes
-
-
-
additional information
?
-
Pseudomonas aeruginosa Travers, Escherichia coli R135/C600
-
no substrates are amikacin
-
-
-
NATURAL SUBSTRATES
NATURAL PRODUCTS
REACTION DIAGRAM
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
(Substrate)
LITERATURE
(Substrate)
COMMENTARY
(Product)
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 ACCESSION NO.
COMMENTARY
LITERATURE
Ca2+
-
1.0 mM, about 100% activity enhancement
Mg2+
-
1.5 mM, about 100% activity enhancement
NH4+
-
slight activation
INHIBITORS
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
IMAGE
3-(dimethylamino)propylamine
-
0.5 mM, 30% residual activity
acetyltobramycin
-
-
Butyryl-CoA
-
dead-end inhibition pattern
CoA
-
product inhibition
desulfo-CoA
-, Q306W4
-
EDTA
-
above 0.5 mM
gentamicin C1a
-
substrate inhibition
kanamycin A
-
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
netilmicin
-, Q306W4
-
ribostamycin
-
substrate inhibition
tobramycin
-
substrate inhibition
kanamycin B
-
substrate inhibition
additional information
-
no inhibition by NH4+, K+, Na+, DTT, N-methylmaleimide
-
additional information
-
inhibition kinetics
-
additional information
-
only small aminoglycosides without intraring constraints show substrate inhibition
-
KM VALUE [mM]
KM VALUE [mM] Maximum
SUBSTRATE
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
IMAGE
0.0013
-
acetyl-CoA
-
cosubstrate gentamicin C1a
0.0017
-
acetyl-CoA
-
cosubstrate tobramycin
0.0154
-
acetyl-CoA
-
cosubstrate kanamycin A, pH 7.6, 25C
0.086
-
acetyl-CoA
-, Q306W4
in 50 mM HEPES, pH 7.5 and 0.1 mM 4,4'-dithiodipyridine, at pH 7.8 and 25C
0.17
-
acetyl-CoA
-
cosubstrate neomycin B, pH 7.6, 25C
0.00096
-
amikacin
-
pH 6.6, with acetyl-CoA, His-tagged enzyme expressed from vector pET22b
0.0021
-
amikacin
-
pH 6.6, with n-propionyl-CoA, His-tagged enzyme expressed from vector pET22b
0.0716
-
amikacin
-
pH 6.6, with malonyl-CoA, His-tagged enzyme expressed from vector pET22b
11.07
-
amikacin
-, Q306W4
in 50 mM HEPES, pH 7.5 and 0.1 mM 4,4'-dithiodipyridine, at pH 7.8 and 25C
0.00067
-
apramycin
-, Q306W4
in 50 mM HEPES, pH 7.5 and 0.1 mM 4,4'-dithiodipyridine, at pH 7.8 and 25C
0.237
-
butirosin
-, Q306W4
in 50 mM HEPES, pH 7.5 and 0.1 mM 4,4'-dithiodipyridine, at pH 7.8 and 25C
1.16
-
Butyryl-CoA
-, Q306W4
in 50 mM HEPES, pH 7.5 and 0.1 mM 4,4'-dithiodipyridine, at pH 7.8 and 25C
0.0029
-
gentamicin
-
pH 6.6, with n-propionyl-CoA, His-tagged enzyme expressed from vector pET22b
0.0046
-
gentamicin
-
pH 6.6, with acetyl-CoA, His-tagged enzyme expressed from vector pET22b
0.0189
-
gentamicin
-
pH 6.6, with malonyl-CoA, His-tagged enzyme expressed from vector pET22b
0.066
-
gentamicin C1
-
-
0.00012
-
gentamicin C1a
-
-
0.00097
-
gentamycin
-, Q306W4
in 50 mM HEPES, pH 7.5 and 0.1 mM 4,4'-dithiodipyridine, at pH 7.8 and 25C
0.002
-
kanamycin A
-
pH 6.6, with acetyl-CoA, His-tagged enzyme expressed from vector pET28a
0.0033
-
kanamycin A
-
pH 6.6, with acetyl-CoA, His-tagged enzyme expressed from vector Int-pET19b-pps
0.0048
-
kanamycin A
-
pH 6.6, with n-propionyl-CoA, His-tagged enzyme expressed from vector pET28a
0.0048
-
kanamycin A
-
pH 7.6, 25C
0.0055
-
kanamycin A
-
pH 6.6, with acetyl-CoA, His-tagged enzyme expressed from vector pET22b
0.0091
-
kanamycin A
-
pH 6.6, with n-propionyl-CoA, His-tagged enzyme expressed from vector Int-pET19b-pps
0.0099
-
kanamycin A
-
pH 6.6, with acetyl-CoA, untagged enzyme expressed from vector Int-pET19b-pps
0.0111
-
kanamycin A
-
pH 6.6, with n-propionyl-CoA, His-tagged enzyme expressed from vector pET22b
0.0135
-
kanamycin A
-
pH 6.6, with n-propionyl-CoA, untagged enzyme expressed from vector Int-pET19b-pps
0.238
-
kanamycin A
-, Q306W4
in 50 mM HEPES, pH 7.5 and 0.1 mM 4,4'-dithiodipyridine, at pH 7.8 and 25C
0.0026
-
kanamycin B
-
pH 7.6, 25C
0.0036
-
lividomycin A
-
pH 7.6, 25C
0.234
-
malonyl-CoA
-
cosubstrate kanamycin A, pH 7.6, 25C
0.0886
-
n-propionyl-CoA
-
cosubstrate kanamycin A, pH 7.6, 25C
0.00036
-
neomycin
-, Q306W4
in 50 mM HEPES, pH 7.5 and 0.1 mM 4,4'-dithiodipyridine, at pH 7.8 and 25C
0.0012
-
neomycin B
-
pH 7.6, 25C
0.0031
-
neomycin B
-
pH 6.6, with n-propionyl-CoA, His-tagged enzyme expressed from vector pET22b
0.0148
-
neomycin B
-
pH 6.6, with acetyl-CoA, His-tagged enzyme expressed from vector pET22b
0.042
-
netilmicin
-, Q306W4
in 50 mM HEPES, pH 7.5 and 0.1 mM 4,4'-dithiodipyridine, at pH 7.8 and 25C
0.00015
-
paromomycin
-, Q306W4
in 50 mM HEPES, pH 7.5 and 0.1 mM 4,4'-dithiodipyridine, at pH 7.8 and 25C
0.0033
-
paromomycin
-
pH 7.6, 25C
0.499
-
propionyl-CoA
-, Q306W4
in 50 mM HEPES, pH 7.5 and 0.1 mM 4,4'-dithiodipyridine, at pH 7.8 and 25C
0.0023
-
ribostamycin
-
pH 7.6, 25C
0.0031
-
ribostamycin
-, Q306W4
in 50 mM HEPES, pH 7.5 and 0.1 mM 4,4'-dithiodipyridine, at pH 7.8 and 25C
0.00057
-
sisomicin
-
pH 6.6, with n-propionyl-CoA, His-tagged enzyme expressed from vector pET22b
0.000724
-
sisomicin
-
pH 7.2, 34C
0.0015
-
sisomicin
-
pH 6.6, with acetyl-CoA, His-tagged enzyme expressed from vector pET22b
0.00033
-
sisomycin
-, Q306W4
in 50 mM HEPES, pH 7.5 and 0.1 mM 4,4'-dithiodipyridine, at pH 7.8 and 25C
0.0015
-
sisomycin
-
pH 7.6, 25C
0.0013
-
tobramycin
-
pH 7.6, 25C
0.00142
-
tobramycin
-, Q306W4
in 50 mM HEPES, pH 7.5 and 0.1 mM 4,4'-dithiodipyridine, at pH 7.8 and 25C
0.0016
-
tobramycin
-
-
0.0027
-
tobramycin
-
pH 6.6, with acetyl-CoA, His-tagged enzyme expressed from vector pET22b
0.0054
-
tobramycin
-
pH 6.6, with n-propionyl-CoA, His-tagged enzyme expressed from vector pET22b
0.477
-
malonyl-CoA
-, Q306W4
in 50 mM HEPES, pH 7.5 and 0.1 mM 4,4'-dithiodipyridine, at pH 7.8 and 25C
additional information
-
additional information
-
kinetic pattern
-
TURNOVER NUMBER [1/s]
TURNOVER NUMBER MAXIMUM[1/s]
SUBSTRATE
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
IMAGE
10.5
-
acetyl-CoA
-
cosubstrate neomycin B, pH 7.6, 25C
39
-
acetyl-CoA
-, Q306W4
in 50 mM HEPES, pH 7.5 and 0.1 mM 4,4'-dithiodipyridine, at pH 7.8 and 25C
39.4
-
acetyl-CoA
-
cosubstrate kanamycin A, pH 7.6, 25C
0.124
-
amikacin
-
pH 6.6, with n-propionyl-CoA, His-tagged enzyme expressed from vector pET22b
0.126
-
amikacin
-
pH 6.6, with acetyl-CoA, His-tagged enzyme expressed from vector pET22b
0.146
-
amikacin
-
pH 6.6, with malonyl-CoA, His-tagged enzyme expressed from vector pET22b
0.5
-
amikacin
-, Q306W4
in 50 mM HEPES, pH 7.5 and 0.1 mM 4,4'-dithiodipyridine, at pH 7.8 and 25C
61
-
apramycin
-, Q306W4
in 50 mM HEPES, pH 7.5 and 0.1 mM 4,4'-dithiodipyridine, at pH 7.8 and 25C
3.5
-
butirosin
-, 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
-, Q306W4
in 50 mM HEPES, pH 7.5 and 0.1 mM 4,4'-dithiodipyridine, at pH 7.8 and 25C
0.041
-
gentamicin
-
pH 6.6, with malonyl-CoA, His-tagged enzyme expressed from vector pET22b
0.123
-
gentamicin
-
pH 6.6, with n-propionyl-CoA, His-tagged enzyme expressed from vector pET22b
0.182
-
gentamicin
-
pH 6.6, with acetyl-CoA, His-tagged enzyme expressed from vector pET22b
40
-
gentamycin
-, Q306W4
in 50 mM HEPES, pH 7.5 and 0.1 mM 4,4'-dithiodipyridine, at pH 7.8 and 25C
0.012
-
kanamycin A
-
pH 6.6, with acetyl-CoA, His-tagged enzyme expressed from vector pET28a
0.017
-
kanamycin A
-
pH 6.6, with n-propionyl-CoA, His-tagged enzyme expressed from vector pET28a
0.044
-
kanamycin A
-
pH 6.6, with n-propionyl-CoA, His-tagged enzyme expressed from vector Int-pET19b-pps
0.134
-
kanamycin A
-
pH 6.6, with n-propionyl-CoA, His-tagged enzyme expressed from vector pET22b
0.144
-
kanamycin A
-
pH 6.6, with n-propionyl-CoA, untagged enzyme expressed from vector Int-pET19b-pps
0.163
-
kanamycin A
-
pH 6.6, with acetyl-CoA, His-tagged enzyme expressed from vector Int-pET19b-pps
0.3
-
kanamycin A
-
pH 6.6, with acetyl-CoA, His-tagged enzyme expressed from vector pET22b
0.559
-
kanamycin A
-
pH 6.6, with acetyl-CoA, untagged enzyme expressed from vector Int-pET19b-pps
51.4
-
kanamycin A
-
pH 7.6, 25C
80
-
kanamycin A
-, Q306W4
in 50 mM HEPES, pH 7.5 and 0.1 mM 4,4'-dithiodipyridine, at pH 7.8 and 25C
54.5
-
kanamycin B
-
pH 7.6, 25C
33.8
-
lividomycin A
-
pH 7.6, 25C
5.7
-
malonyl-CoA
-
cosubstrate kanamycin A, pH 7.6, 25C
9
-
malonyl-CoA
-, Q306W4
in 50 mM HEPES, pH 7.5 and 0.1 mM 4,4'-dithiodipyridine, at pH 7.8 and 25C
10.2
-
n-propionyl-CoA
-
cosubstrate kanamycin A, pH 7.6, 25C
60
-
neomycin
-, Q306W4
in 50 mM HEPES, pH 7.5 and 0.1 mM 4,4'-dithiodipyridine, at pH 7.8 and 25C
0.076
-
neomycin B
-
pH 6.6, with n-propionyl-CoA, His-tagged enzyme expressed from vector pET22b
0.188
-
neomycin B
-
pH 6.6, with acetyl-CoA, His-tagged enzyme expressed from vector pET22b
9.5
-
neomycin B
-
pH 7.6, 25C
32
-
netilmicin
-, Q306W4
in 50 mM HEPES, pH 7.5 and 0.1 mM 4,4'-dithiodipyridine, at pH 7.8 and 25C
15
-
paromomycin
-, Q306W4
in 50 mM HEPES, pH 7.5 and 0.1 mM 4,4'-dithiodipyridine, at pH 7.8 and 25C
33.6
-
paromomycin
-
pH 7.6, 25C
33
-
propionyl-CoA
-, Q306W4
in 50 mM HEPES, pH 7.5 and 0.1 mM 4,4'-dithiodipyridine, at pH 7.8 and 25C
23.5
-
ribostamycin
-
pH 7.6, 25C
146
-
ribostamycin
-, Q306W4
in 50 mM HEPES, pH 7.5 and 0.1 mM 4,4'-dithiodipyridine, at pH 7.8 and 25C
0.121
-
sisomicin
-
pH 6.6, with n-propionyl-CoA, His-tagged enzyme expressed from vector pET22b
0.173
-
sisomicin
-
pH 6.6, with acetyl-CoA, His-tagged enzyme expressed from vector pET22b
46.3
-
sisomycin
-
pH 7.6, 25C
51
-
sisomycin
-, Q306W4
in 50 mM HEPES, pH 7.5 and 0.1 mM 4,4'-dithiodipyridine, at pH 7.8 and 25C
0.089
-
tobramycin
-
pH 6.6, with n-propionyl-CoA, His-tagged enzyme expressed from vector pET22b
0.179
-
tobramycin
-
pH 6.6, with acetyl-CoA, His-tagged enzyme expressed from vector pET22b
47.8
-
tobramycin
-
pH 7.6, 25C
162
-
tobramycin
-, Q306W4
in 50 mM HEPES, pH 7.5 and 0.1 mM 4,4'-dithiodipyridine, at pH 7.8 and 25C
kcat/KM VALUE [1/mMs-1]
kcat/KM VALUE [1/mMs-1] Maximum
SUBSTRATE
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
IMAGE
600
-
acetyl-CoA
-
cosubstrate neomycin B, pH 7.6, 25C
6194
2600
-
acetyl-CoA
-
cosubstrate kanamycin A, pH 7.6, 25C
6194
11200
-
kanamycin A
-
pH 7.6, 25C
11896
34400
-
kanamycin B
-
pH 7.6, 25C
11897
9500
-
lividomycin A
-
pH 7.6, 25C
218132
30
-
malonyl-CoA
-
cosubstrate kanamycin A, pH 7.6, 25C
12844
120
-
n-propionyl-CoA
-
cosubstrate kanamycin A, pH 7.6, 25C
14077
9100
-
neomycin B
-
pH 7.6, 25C
14429
10800
-
paromomycin
-
pH 7.6, 25C
15221
10600
-
ribostamycin
-
pH 7.6, 25C
16209
33400
-
sisomycin
-
pH 7.6, 25C
146755
60500
-
tobramycin
-
pH 7.6, 25C
17222
Ki VALUE [mM]
Ki VALUE [mM] Maximum
INHIBITOR
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
IMAGE
0.381
-
kanamycin A
-
pH 7.6, 25C
0.0059
-
ribostamycin
-
pH 7.6, 25C
SPECIFIC ACTIVITY [µmol/min/mg]
SPECIFIC ACTIVITY MAXIMUM
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
9.743
-
-
pH 7.2, 34C
additional information
-
-
Vmax 0.102 (sisomicin), pH 7.2, 34C
pH OPTIMUM
pH MAXIMUM
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
6.6
-
-
assay at
8
-
-, Q306W4
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
TEMPERATURE OPTIMUM MAXIMUM
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
25
-
-
assay at
37
-
-
assay at
pI VALUE
pI VALUE MAXIMUM
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
5.7
-
-, Q306W4
calculated from amino acid sequence
LOCALIZATION
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
GeneOntology No.
LITERATURE
SOURCE
MOLECULAR WEIGHT
MOLECULAR WEIGHT MAXIMUM
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
18630
-
-
18649 Da predicted from nucleotide sequence, 18630 Da found by mass spectrometry
49000
-
Q4R0X5, -
SDS-PAGE
54000
-
-, Q306W4
dynamic light scattering
55750
-
-, Q306W4
calculated from amino acid sequence
60000
-
-, Q306W4
Sephacryl-S200 gel filtration
additional information
-
-
amino acid analysis
SUBUNITS
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
dimer
-, Q306W4
2 * 28000, enzyme in solution
dimer
Escherichia coli BL21(DE3) pLysS
-
2 * 28000, enzyme in solution
-
POSTTRANSLATIONAL MODIFICATION
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
side-chain modification
-
cleavage of the hexahistidine tag by tobacco etch virus protease
Crystallization/COMMENTARY
ORGANISM
UNIPROT ACCESSION NO.
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
TEMPERATURE STABILITY MAXIMUM
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
40
-
-
above, inactivation within 2 min
GENERAL STABILITY
ORGANISM
UNIPROT ACCESSION NO.
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 ACCESSION NO.
LITERATURE
-20C, partially purified, several months
-
-20C, purified, several days
-
Purification/COMMENTARY
ORGANISM
UNIPROT ACCESSION NO.
LITERATURE
Fast Flow Q-Sepharose anion exchange column chromatography and Phenyl Sepharose column chromatography
-, Q306W4
plasmid pPK237 transferred to and expressed in E. coli K12, affinity chromatography
-
Ni2+-affinity chromatography
Q4R0X5, -
Cloned/COMMENTARY
ORGANISM
UNIPROT ACCESSION NO.
LITERATURE
expression in Escherichia coli K802N by mating
Arizona sp.
-
expressed in the pET-23a(+) expression vector
-, Q306W4
expression of C- or N-terminally His-tagged enzyme from vectors pET22b, and pET28a or Int-pET19b-pps, respectively
-
expressed in Escherichia coli
-
expression in Escherichia coli K802N by mating
-
expression in Escherichia coli
-
expression in Escherichia coli DH5alpha
Q83V16
Pseudomonas aeruginosa plasmid pPK237 transferred to and expressed in Escherichia coli K12
-
gene aac(3)-Id, in a class 1 integron
-
wild-type and truncated enzymes expressed in Escherichia coli
-
plasmid transfer pIJ702 to Streptomyces lividans TK21
-
expressed in Escherichia coli
Q4R0X5, -
APPLICATION
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
medicine
Arizona sp., Escherichia coli
-
studies on the novel aminoglycoside antibiotic apramycin
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
medicine
-
studies on the novel aminoglycoside antibiotic apramycin
medicine
-
mutation in the gene promoter affects the transcription level and enhances resistance to antibiotics