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Information on EC 2.7.7.46 - gentamicin 2''-nucleotidyltransferase
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2.7.7.46 gentamicin 2''-nucleotidyltransferaseIUBMB Comments
ATP, dATP, CTP, ITP and GTP can act as donors; kanamycin, tobramycin and sisomicin can also act as acceptors. The nucleotidyl residue is transferred to the 2-hydroxy of the 3-amino-3-deoxy-D-glucose moiety in the antibiotic.
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Word Map
- 2.7.7.46
-
aac3-ii
- tobramycin
- colistin
- integrons
-
nucleotidylated
-
aminoglycoside-modifying
-
aac6'-ie
-
aph3\'-vi
- amikacin
-
extended-spectrum
-
esbls
- medicine
-
theorell-chance
- blandm-1
-
northrop
-
colistin-resistant
-
co-harboured
-
genre
- carbapenemases
-
gentamicin-resistant
- netilmicin
The enzyme appears in viruses and cellular organisms
Synonyms
ant(2'')-i, ant(2'')-ia, aminoglycoside nucleotidyltransferase 2''-i, gentamicin nucleotidyltransferase, 
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SYNONYM 
ORGANISM
UNIPROT
COMMENTARY 
LITERATURE
aadB
aadB(ant2')Ia
aminoglycoside adenylyltransferase
aminoglycoside nucleotidyltransferase 2''-I
ANT(2'')-I
gentamicin 2''-adenylyltransferase
-
-
-
-
gentamicin nucleotidyltransferase
-
-
-
-
aminoglycoside adenylyltransferase
-
-
-
-
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REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
nucleoside triphosphate + gentamicin = diphosphate + 2''-nucleotidylgentamicin
ATP, dATP, CTP, ITP and GTP can act as donors
-
-
-
nucleoside triphosphate + gentamicin = diphosphate + 2''-nucleotidylgentamicin
kanamycin, tobramycin and sisomicin can also act as acceptors. The nucleotidyl residue is transferred to the 2-hydroxy of the 3-amino-3-deoxy-D-glucose moiety in the antibiotic
-
-
-
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REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
nucleotidyl group transfer
-
-
-
-
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SYSTEMATIC NAME
IUBMB Comments
NTP:gentamicin 2''-nucleotidyltransferase
ATP, dATP, CTP, ITP and GTP can act as donors; kanamycin, tobramycin and sisomicin can also act as acceptors. The nucleotidyl residue is transferred to the 2-hydroxy of the 3-amino-3-deoxy-D-glucose moiety in the antibiotic.
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CAS REGISTRY NUMBER
COMMENTARY
62213-33-6
-
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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
adenosine 5'-mono-O-phosphorothiolate + tobramycin
diphosphate + 2''-(adenosine-5'-thiophosphoryl)-tobramycin
-
-
-
-
r
ATP + gentamicin C2
diphosphate + 2''-adenylylgentamicin C2
-
gentamicin A, C1, C1a, or C2 can act as acceptors, dATP, CTP, ITP or GTP can act as donors
-
-
?
ATP + tobramycin
diphosphate + 2''-(adenosine-5'-phosphoryl)-tobramycin
-
-
-
-
r
additional information
?
-
-
amikacin, neomycin, lividomycin and butirosin A and B are no substrates
-
-
?
ATP + dideoxykanamycin B
diphosphate + 3',4'-dideoxykanamycin B-2''-adenylate
-
adenylates the 2-hydroxyl group of the 3-amino-3-deoxy-D-glucose moiety
3',4'-dideoxykanamycin B-2''-adenylate
r
ATP + dideoxykanamycin B
diphosphate + 3',4'-dideoxykanamycin B-2''-adenylate
-
adenylates the 2-hydroxyl group of the 3-amino-3-deoxy-D-glucose moiety
3',4'-dideoxykanamycin B-2''-adenylate
r
ATP + dideoxykanamycin B
diphosphate + 3',4'-dideoxykanamycin B-2''-adenylate
-
adenylates the 2-hydroxyl group of the 3-amino-3-deoxy-D-glucose moiety
3',4'-dideoxykanamycin B-2''-adenylate
r
ATP + dideoxykanamycin B
diphosphate + 3',4'-dideoxykanamycin B-2''-adenylate
-
adenylates the 2-hydroxyl group of the 3-amino-3-deoxy-D-glucose moiety
3',4'-dideoxykanamycin B-2''-adenylate
r
ATP + gentamicin
diphosphate + 2''-adenylylgentamicin
-
-
-
?
ATP + gentamicin A
diphosphate + 2''-adenylylgentamicin A
-
gentamicin A, C1 and C1a, MgATP2-, MgdATP2- and MgdGTP2- can act as donors
-
-
r
ATP + gentamicin A
diphosphate + 2''-adenylylgentamicin A
-
gentamicin A, C1 and C1a, MgATP2-, MgdATP2- and MgdGTP2- can act as donors
-
-
r
ATP + gentamicin A
diphosphate + 2''-adenylylgentamicin A
-
gentamicin A, C1, C1a, or C2 can act as acceptors, dATP, CTP, ITP or GTP can act as donors
-
r
ATP + gentamicin C1
diphosphate + 2''-adenylylgentamicin C1
-
gentamicin A, C1 and C1a, MgATP2-, MgdATP2- and MgdGTP2- can act as donors
-
-
?
ATP + gentamicin C1
diphosphate + 2''-adenylylgentamicin C1
-
gentamicin A, C1 and C1a, MgATP2-, MgdATP2- and MgdGTP2- can act as donors
-
-
?
ATP + gentamicin C1
diphosphate + 2''-adenylylgentamicin C1
-
gentamicin A, C1, C1a, or C2 can act as acceptors, dATP, CTP, ITP or GTP can act as donors
-
-
?
ATP + gentamicin C1a
diphosphate + 2''-adenylylgentamicin C1a
-
gentamicin A, C1 and C1a, MgATP2-, MgdATP2- and MgdGTP2- can act as donors
-
-
?
ATP + gentamicin C1a
diphosphate + 2''-adenylylgentamicin C1a
-
gentamicin A, C1, C1a, or C2 can act as acceptors, dATP, CTP, ITP or GTP can act as donors
-
-
?
ATP + kanamycin A
diphosphate + 2''-adenylylkanamycin A
-
poor substrate
-
-
r
ATP + tobramycin
diphosphate + 2''-adenylyltobramycin
-
-
-
-
r
ATP + tobramycin
diphosphate + 2''-adenylyltobramycin
-
poor substrate
-
-
r
nucleoside triphosphate + gentamicin
diphosphate + 2''-nucleotidylgentamicin
-
-
-
?
nucleoside triphosphate + gentamicin
diphosphate + 2''-nucleotidylgentamicin
-
-
-
?
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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
ATP + gentamicin A
diphosphate + 2''-adenylylgentamicin A
-
gentamicin A, C1, C1a, or C2 can act as acceptors, dATP, CTP, ITP or GTP can act as donors
-
r
nucleoside triphosphate + gentamicin
diphosphate + 2''-nucleotidylgentamicin
-
-
-
?
nucleoside triphosphate + gentamicin
diphosphate + 2''-nucleotidylgentamicin
-
-
-
?
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METALS and IONS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
Ca2+
-
shows enzymatic activity only in presence of cations, optimal concentration 1.0 mM
Mg2+
additional information
-
K+ and Na+ have almost no effect, NH4+ has a low enhancing effect
Mg2+
-
shows enzymatic activity only in presence of cations, optimal concentration 2.0 mM
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INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
MgATP2-
-
metal chelates being the true substrates, free nucleotides being inhibitors
MgCTP2-
-
metal chelates being the true substrates, free nucleotides being inhibitors
MgdATP2-
-
metal chelates being the true substrates, free nucleotides being inhibitors
MgdCTP2-
-
metal chelates being the true substrates, free nucleotides being inhibitors
MgdGTP2-
-
metal chelates being the true substrates, free nucleotides being inhibitors
MgdTTP2-
-
metal chelates being the true substrates, free nucleotides being inhibitors
MgGTP2-
-
metal chelates being the true substrates, free nucleotides being inhibitors
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DISEASE
TITLE OF PUBLICATION
LINK TO PUBMED
Gram-Negative Bacterial Infections
Purification and properties of gentamicin nucleotidyltransferase from Escherichia coli: nucleotide specificity, pH optimum, and the separation of two electrophoretic variants.
Infections
Co-occurrence of clinically relevant ?-lactamases and MCR-1 encoding genes in Escherichia coli from companion animals in Argentina.
Urinary Tract Infections
Co-occurrence of clinically relevant ?-lactamases and MCR-1 encoding genes in Escherichia coli from companion animals in Argentina.
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KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
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Ki VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
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SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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pH RANGE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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pI VALUE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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ORGANISM
COMMENTARY
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
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LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY
GeneOntology No.
LITERATURE
SOURCE
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UNIPROT
ENTRY NAME
ORGANISM
NO. OF AA
NO. OF TRANSM. HELICES
MOLECULAR WEIGHT[Da]
SOURCE
SEQUENCE
LOCALIZATION PREDICTION
The reliability class of the localization prediction ranges from 1 (very reliable) to 5 (not reliable).
The reliability class of the localization prediction ranges from 1 (very reliable) to 5 (not reliable). Q75WE9_9ZZZZ
253
0
28860
TrEMBL
other Location (Reliability: 2)
A0A0J0ZZP3_ACIBA
181
0
20305
TrEMBL
-
T1Y4G6_STAAU
256
0
29166
TrEMBL
-
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PDB
SCOP
CATH
UNIPROT
ORGANISM
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MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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SUBUNIT
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
monomer
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PROTEIN VARIANTS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
D44A
the mutation causes a 4fold decrease in aminoglycoside adenylation compared to the wild type enzyme
I129A
the mutation causes a 3fold decrease in aminoglycoside adenylation compared to the wild type enzyme
Y135A
the mutation causes a 1.6fold decrease in aminoglycoside adenylation compared to the wild type enzyme
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GENERAL STABILITY
ORGANISM
UNIPROT
LITERATURE
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STORAGE STABILITY
ORGANISM
UNIPROT
LITERATURE
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PURIFICATION (Commentary)
ORGANISM
UNIPROT
LITERATURE
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CLONED (Commentary)
ORGANISM
UNIPROT
LITERATURE
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EXPRESSION
ORGANISM
UNIPROT
LITERATURE
tobramycin-resistant subpopulations of Acinetobacter baumannii exhibit increased enzyme expression
tobramycin-resistant subpopulations of Acinetobacter baumannii exhibit increased enzyme expression
tobramycin-resistant subpopulations of Acinetobacter baumannii exhibit increased enzyme expression
-
-
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APPLICATION
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
medicine
medicine
-
gentamicin resistance, mediated by multiple resistance plasmids in different species of Enterobacteriaceae, can be a problem in hospitals
medicine
-
studies should aid in the design of effective inhibitors possessing a broad range of aminoglycoside-modifying enzymes as targets
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REF.
AUTHORS
TITLE
JOURNAL
VOL.
PAGES
YEAR
ORGANISM (UNIPROT)
PUBMED ID
SOURCE
Angelatou, F.; Litsas, S.B.; Kontomichalou, P.
Purification and properties of two gentamicin-modifying enzymes, coded by a single plasmid pPK237 originating from Pseudomonas aeruginosa
J. Antibiot.
35
235-244
1982
Pseudomonas aeruginosa
brenda
Van Pelt, J.E.; Northrop, D.B.
Purification and properties of gentamicin nucleotidyltransferase from Escherichia coli: nucleotide specificity, pH optimum, and the separation of two electrophoretic variants
Arch. Biochem. Biophys.
230
250-263
1984
Escherichia coli
brenda
Yagisawa, M.; Naganawa, H.; Kondo, S.; Hamada, M.; Takeuchi, T.; Umezawa, H.
Adenylyldideoxykanamycin B, a product of the inactivation of dideoxykanamycin B by Escherichia coli carrying R factor
J. Antibiot.
26
911-912
1971
Escherichia coli, Escherichia coli JR66/W677
-
brenda
Naganawa, H.; Yagisawa, M.; Kondo, S.; Takeuchi, T.; Umezawa, H.
The structure determination of an enzymatic inactivation product of 3',4'-dideoxykanamycin B
J. Antibiot.
26
913-914
1971
Escherichia coli, Escherichia coli JR66/W677
brenda
Gates, C.A.; Northrop, D.B.
Alternative substrate and inhibition kinetics of aminoglycoside nucleotidyltransferase 2''-I in support of a Theorell-Chance kinetic mechanism
Biochemistry
27
3826-3833
1988
Escherichia coli, Escherichia coli W677/pMY10
brenda
Gates, C.A.; Northrop, D.B.
Determination of the rate-limiting segment of aminoglycoside nucleotidyltransferase 2''-I by pH- and viscosity-dependent kinetics
Biochemistry
27
3834-3842
1988
Escherichia coli
brenda
Van Pelt, J.E.; Mooberry, E.S.; Frey, P.A.
1H, 13C, and 31P nuclear magnetic resonance spectral assignments for tobramycin, 2"-(adenosine-5'-phosphoryl)-tobramycin and 2"-(adenosine-5'-thiophosphoryl)-tobramycin
Arch. Biochem. Biophys.
280
284-291
1990
Escherichia coli
brenda
Ekman, D.R.; DiGiammarino, E.L.; Wright, E.; Witter, E.D.; Serpersu, E.H.
Cloning, overexpression, and purification of aminoglycoside antibiotic nucleotidyltransferase (2'')-Ia: conformational studies with bound substrates
Biochemistry
40
7017-7024
2001
Pseudomonas aeruginosa
brenda
Anderson, S.E.; Sherman, E.X.; Weiss, D.S.; Rather, P.N.
Aminoglycoside heteroresistance in Acinetobacter baumannii AB5075
mSphere
3
e00271-18
2018
Acinetobacter baumannii (B0VCJ4), Acinetobacter baumannii AB5075 (B0VCJ4)
brenda
Bacot-Davis, V.R.; Bassenden, A.V.; Sprules, T.; Berghuis, A.M.
Effect of solvent and protein dynamics in ligand recognition and inhibition of aminoglycoside adenyltransferase 2''-Ia
Protein Sci.
26
1852-1863
2017
Klebsiella pneumoniae (P0AE05)
brenda
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