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PDBsum entry 2et3
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Nucleic Acids Res
33:5677-5690
(2005)
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PubMed id:
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Crystal structures of complexes between aminoglycosides and decoding A site oligonucleotides: role of the number of rings and positive charges in the specific binding leading to miscoding.
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B.François,
R.J.Russell,
J.B.Murray,
F.Aboul-ela,
B.Masquida,
Q.Vicens,
E.Westhof.
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ABSTRACT
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The crystal structures of six complexes between aminoglycoside antibiotics
(neamine, gentamicin C1A, kanamycin A, ribostamycin, lividomycin A and neomycin
B) and oligonucleotides containing the decoding A site of bacterial ribosomes
are reported at resolutions between 2.2 and 3.0 A. Although the number of
contacts between the RNA and the aminoglycosides varies between 20 and 31, up to
eight direct hydrogen bonds between rings I and II of the neamine moiety are
conserved in the observed complexes. The puckered sugar ring I is inserted into
the A site helix by stacking against G1491 and forms a pseudo base pair with two
H-bonds to the Watson-Crick sites of the universally conserved A1408. This
central interaction helps to maintain A1492 and A1493 in a bulged-out
conformation. All these structures of the minimal A site RNA complexed to
various aminoglycosides display crystal packings with intermolecular contacts
between the bulging A1492 and A1493 and the shallow/minor groove of Watson-Crick
pairs in a neighbouring helix. In one crystal, one empty A site is observed. In
two crystals, two aminoglycosides are bound to the same A site with one bound
specifically and the other bound in various ways in the deep/major groove at the
edge of the A sites.
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Literature references that cite this PDB file's key reference
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PubMed id
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Reference
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PDB codes:
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PLoS One,
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A model for the study of ligand binding to the ribosomal RNA helix h44.
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Nucleic Acids Res,
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PDB code:
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S.Y.Chen,
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A molecular dynamics study on binding recognition between several 4,5 and 4,6-linked aminoglycosides with A-site RNA.
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J Mol Recognit,
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Biochemistry,
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Y.Xie,
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Chem Commun (Camb),
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Two-dimensional combinatorial screening and the RNA Privileged Space Predictor program efficiently identify aminoglycoside-RNA hairpin loop interactions.
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Nucleic Acids Res,
37,
5894-5907.
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E.Diago-Navarro,
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M.Lemonnier
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Novel Escherichia coli RF1 mutants with decreased translation termination activity and increased sensitivity to the cytotoxic effect of the bacterial toxins Kid and RelE.
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Mol Microbiol,
71,
66-78.
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I.A.Katsoulis,
C.Pyrkotis,
A.Papakyriakou,
G.Kythreoti,
A.L.Zografos,
I.Mavridis,
V.R.Nahmias,
P.Anastasopoulou,
and
D.Vourloumis
(2009).
Unnatural rigid scaffolds targeting the bacterial ribosome.
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Chembiochem,
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M.Chittapragada,
S.Roberts,
and
Y.W.Ham
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Aminoglycosides: molecular insights on the recognition of RNA and aminoglycoside mimics.
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Perspect Medicin Chem,
3,
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M.J.Belousoff,
B.Graham,
L.Spiccia,
and
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Cleavage of RNA oligonucleotides by aminoglycosides.
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Org Biomol Chem,
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P.G.Young,
R.Walanj,
V.Lakshmi,
L.J.Byrnes,
P.Metcalf,
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J Bacteriol,
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PDB codes:
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P.Setny,
and
J.Trylska
(2009).
Search for novel aminoglycosides by combining fragment-based virtual screening and 3D-QSAR scoring.
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and
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W.G.Scott,
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Crystal structure of a translation termination complex formed with release factor RF2.
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Proc Natl Acad Sci U S A,
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PDB codes:
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C.Bauder
(2008).
A convenient synthesis of orthogonally protected 2-deoxystreptamine (2-DOS) as an aminocyclitol scaffold for the development of novel aminoglycoside antibiotic derivatives against bacterial resistance.
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Org Biomol Chem,
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D.Balenci,
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N.D'Amelio,
E.Gaggelli,
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and
G.Valensin
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Effect of Cu(II) on the complex between kanamycin A and the bacterial ribosomal A site.
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Chembiochem,
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D.W.Staple,
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Y.Tor,
and
S.E.Butcher
(2008).
Guanidinoneomycin B recognition of an HIV-1 RNA helix.
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Chembiochem,
9,
93.
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PDB code:
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J.E.Weigand,
M.Sanchez,
E.B.Gunnesch,
S.Zeiher,
R.Schroeder,
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RNA,
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J.Kondo,
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The bacterial and mitochondrial ribosomal A-site molecular switches possess different conformational substates.
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Nucleic Acids Res,
36,
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PDB codes:
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J.Romanowska,
P.Setny,
and
J.Trylska
(2008).
Molecular dynamics study of the ribosomal A-site.
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J Phys Chem B,
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L.Wu,
P.G.Czyryca,
D.Li,
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Surprising alteration of antibacterial activity of 5"-modified neomycin against resistant bacteria.
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J Med Chem,
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M.Hainrichson,
I.Nudelman,
and
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Designer aminoglycosides: the race to develop improved antibiotics and compounds for the treatment of human genetic diseases.
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Org Biomol Chem,
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Two-dimensional combinatorial screening identifies specific 6'-acylated kanamycin A- and 6'-acylated neamine-RNA hairpin interactions.
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Biochemistry,
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O.J.Barrett,
A.Pushechnikov,
M.Wu,
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Studying aminoglycoside modification by the acetyltransferase class of resistance-causing enzymes via microarray.
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Carbohydr Res,
343,
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C.M.Barbieri,
M.Kaul,
and
D.S.Pilch
(2007).
Use of 2-aminopurine as a fluorescent tool for characterizing antibiotic recognition of the bacterial rRNA A-site.
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Tetrahedron,
63,
3567-6574.
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C.M.Barbieri,
M.Kaul,
M.Bozza-Hingos,
F.Zhao,
Y.Tor,
T.Hermann,
and
D.S.Pilch
(2007).
Defining the molecular forces that determine the impact of neomycin on bacterial protein synthesis: importance of the 2'-amino functionality.
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Antimicrob Agents Chemother,
51,
1760-1769.
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C.Possoz,
J.Newmark,
N.Sorto,
D.J.Sherratt,
and
M.E.Tolmasky
(2007).
Sublethal concentrations of the aminoglycoside amikacin interfere with cell division without affecting chromosome dynamics.
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Antimicrob Agents Chemother,
51,
252-256.
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J.Kondo,
K.Pachamuthu,
B.François,
J.Szychowski,
S.Hanessian,
and
E.Westhof
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Crystal Structure of the Bacterial Ribosomal Decoding Site Complexed with a Synthetic Doubly Functionalized Paromomycin Derivative: a New Specific Binding Mode to an A-Minor Motif Enhances in vitro Antibacterial Activity.
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ChemMedChem,
2,
1631-1638.
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PDB code:
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J.Kondo,
M.Hainrichson,
I.Nudelman,
D.Shallom-Shezifi,
C.M.Barbieri,
D.S.Pilch,
E.Westhof,
and
T.Baasov
(2007).
Differential selectivity of natural and synthetic aminoglycosides towards the eukaryotic and prokaryotic decoding A sites.
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Chembiochem,
8,
1700-1709.
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PDB codes:
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J.Kondo,
T.Sunami,
and
A.Takénaka
(2007).
The structure of a d(gcGAACgc) duplex containing two consecutive bulged A residues in both strands suggests a molecular switch.
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Acta Crystallogr D Biol Crystallogr,
63,
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PDB code:
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J.Wachino,
K.Shibayama,
H.Kurokawa,
K.Kimura,
K.Yamane,
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N.Shibata,
Y.Ike,
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Novel plasmid-mediated 16S rRNA m1A1408 methyltransferase, NpmA, found in a clinically isolated Escherichia coli strain resistant to structurally diverse aminoglycosides.
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Antimicrob Agents Chemother,
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L.Massa,
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Drug target interaction energies by the kernel energy method in aminoglycoside drugs and ribosomal A site RNA targets.
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Proc Natl Acad Sci U S A,
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Fluorescent pyrimidine ribonucleotide: synthesis, enzymatic incorporation, and utilization.
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J Am Chem Soc,
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Nucleic Acids Res,
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V.J.Muller,
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Stop-codon read-through for patients affected by a lysosomal storage disorder.
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Trends Mol Med,
12,
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E.Ennifar,
J.C.Paillart,
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P.Dumas,
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Targeting the dimerization initiation site of HIV-1 RNA with aminoglycosides: from crystal to cell.
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Nucleic Acids Res,
34,
2328-2339.
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PDB codes:
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J.Kondo,
A.Urzhumtsev,
and
E.Westhof
(2006).
Two conformational states in the crystal structure of the Homo sapiens cytoplasmic ribosomal decoding A site.
|
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Nucleic Acids Res,
34,
676-685.
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PDB code:
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J.Kondo,
B.François,
A.Urzhumtsev,
and
E.Westhof
(2006).
Crystal structure of the Homo sapiens cytoplasmic ribosomal decoding site complexed with apramycin.
|
| |
Angew Chem Int Ed Engl,
45,
3310-3314.
|
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PDB code:
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K.F.Blount,
and
Y.Tor
(2006).
A tale of two targets: differential RNA selectivity of nucleobase-aminoglycoside conjugates.
|
| |
Chembiochem,
7,
1612-1621.
|
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N.Foloppe,
N.Matassova,
and
F.Aboul-Ela
(2006).
Towards the discovery of drug-like RNA ligands?
|
| |
Drug Discov Today,
11,
1019-1027.
|
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S.N.Hobbie,
P.Pfister,
C.Bruell,
P.Sander,
B.François,
E.Westhof,
and
E.C.Böttger
(2006).
Binding of neomycin-class aminoglycoside antibiotics to mutant ribosomes with alterations in the A site of 16S rRNA.
|
| |
Antimicrob Agents Chemother,
50,
1489-1496.
|
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|
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T.Tenson,
and
A.Mankin
(2006).
Antibiotics and the ribosome.
|
| |
Mol Microbiol,
59,
1664-1677.
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The most recent references are shown first.
Citation data come partly from CiteXplore and partly
from an automated harvesting procedure. Note that this is likely to be
only a partial list as not all journals are covered by
either method. However, we are continually building up the citation data
so more and more references will be included with time.
Where a reference describes a PDB structure, the PDB
codes are
shown on the right.
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}
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