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Oxidoreductase PDB id
1d8a
Jmol
Contents
Protein chains
257 a.a. *
Ligands
NAD ×2
TCL ×2
Waters ×119
* Residue conservation analysis
PDB id:
1d8a
Name: Oxidoreductase
Title: E. Coli enoyl reductase/NAD+/triclosan complex
Structure: Enoyl-[acyl-carrier-protein] reductase. Chain: a, b. Ec: 1.3.1.9
Source: Escherichia coli. Organism_taxid: 562
Biol. unit: Tetramer (from PDB file)
Resolution:
2.20Å     R-factor:   0.223     R-free:   0.294
Authors: C.W.Levy,A.Roujeinikova,S.Sedelnikova,P.J.Baker,A.R.Stuitje, A.R.Slabas,D.W.Rice,J.B.Rafferty
Key ref:
C.W.Levy et al. (1999). Molecular basis of triclosan activity. Nature, 398, 383-384. PubMed id: 10201369 DOI: 10.1038/18803
Date:
21-Oct-99     Release date:   28-Oct-99    
PROCHECK
Go to PROCHECK summary
 Headers
 References

Protein chains
Pfam   ArchSchema ?
P0AEK4  (FABI_ECOLI) -  Enoyl-[acyl-carrier-protein] reductase [NADH] FabI
Seq:
Struc: 		262 a.a.
257 a.a.
Key:    PfamA domain  Secondary structure  CATH domain

 Enzyme reactions 
   Enzyme class: E.C.1.3.1.9  - Enoyl-[acyl-carrier-protein] reductase (NADH).
[IntEnz]   [ExPASy]   [KEGG]   [BRENDA]
      Reaction: Acyl-[acyl-carrier-protein] + NAD+ = trans-2,3-dehydroacyl-[acyl- carrier-protein] + NADH
Acyl-[acyl-carrier-protein]
 +
NAD(+)
Bound ligand (Het Group name = NAD)
corresponds exactly 		= trans-2,3-dehydroacyl-[acyl- carrier-protein]
 + NADH
Molecule diagrams generated from .mol files obtained from the KEGG ftp site
 Gene Ontology (GO) functional annotation 
  GO annot!
  Cellular component     membrane   1 term 
  Biological process     metabolic process   7 terms 
  Biochemical function     nucleotide binding     3 terms  

 

 
    reference    
 
 
DOI no: 10.1038/18803 Nature 398:383-384 (1999)
PubMed id: 10201369  
 
 
Molecular basis of triclosan activity.
C.W.Levy, A.Roujeinikova, S.Sedelnikova, P.J.Baker, A.R.Stuitje, A.R.Slabas, D.W.Rice, J.B.Rafferty.
 
  ABSTRACT  
 
No abstract given.

 
  Selected figure(s)  
 
Figure 1.
Figure 1: Triclosan bound to E.coli ENR. a, Fourier map at 2.2 Å resolution (1 contour; coefficients 2|F [o]|-|F [c]|) with the refined structure, from co-crystals of an ENR/NAD^+/triclosan complex that are isomorphous with those formed by an ENR/NAD^+/diazaborine complex^4. Data were collected with 78% completeness to 2.2 Å and R [merge]=0.057. Triclosan was located by difference Fourier analysis and the structure was refined to an R -factor of 0.241 (data in the range 10-2.2 Å; free R -factor, 0.286). Generated using the program O (ref. 8). b, Van der Waals surfaces of the enzyme, NAD^+ and triclosan (O, red; N, blue; S, yellow; C, white; P, orange; Cl, green) calculated at 95% radii, shown as white dots for ENR and NAD^+ and yellow dots for triclosan. A mutation of glycine 93 to valine, shown as magenta dots at 75% radii for the side chain of valine, shows how severe steric clashes would result from overlap of the triclosan and valine surfaces. Produced using SYBYL v5.41 (Tripos). c, Residues G93, M159 and F203 (bright yellow) lead to triclosan resistance; the rest of the enzyme is purple, and triclosan and NAD^+ moieties are coloured as in b. d, Superposition of bound triclosan and a model for the enolate anion substrate intermediate showing how triclosan mimics the substrate by similar binding of part of its phenolic ring and the proposed structure of the bound substrate. The NAD^+ nicotinamide ring and associated ribose are at the back and coloured, like triclosan, as in b; the substrate's carbon atoms are cyan. Predicted locations of the phosphopantetheine arm (ACP) and growing acyl chain (R) of the substrate are marked. c, d, Produced using Midas^9.
 
  The above figure is reprinted by permission from Macmillan Publishers Ltd: Nature (1999, 398, 383-384) copyright 1999.  

Literature references that cite this PDB file's key reference

  PubMed id Reference
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21131331 M.Orsi, M.G.Noro, and J.W.Essex (2011).
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PDB codes: 3pjd 3pje 3pjf
21393229 N.Liu, J.E.Cummings, K.England, R.A.Slayden, and P.J.Tonge (2011).
Mechanism and inhibition of the FabI enoyl-ACP reductase from Burkholderia pseudomallei.
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21402423 T.Møretrø, G.S.Høiby-Pettersen, O.Habimana, E.Heir, and S.Langsrud (2011).
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Signature gene expression profile of triclosan-resistant Escherichia coli.
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Slow-onset inhibition of the FabI enoyl reductase from francisella tularensis: residence time and in vivo activity.
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PDB code: 2jjy
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Triclosan derivatives: towards potent inhibitors of drug-sensitive and drug-resistant Mycobacterium tuberculosis.
  ChemMedChem, 4, 241-248.
PDB codes: 3fne 3fnf 3fng 3fnh
19734171 K.England, C.am Ende, H.Lu, T.J.Sullivan, N.L.Marlenee, R.A.Bowen, S.E.Knudson, D.L.Knudson, P.J.Tonge, and R.A.Slayden (2009).
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Diversity in enoyl-acyl carrier protein reductases.
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Assessment of the acute toxicity of triclosan and methyl triclosan in wastewater based on the bioluminescence inhibition of Vibrio fischeri.
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17055058 G.G.Ying, and R.S.Kookana (2007).
Triclosan in wastewaters and biosolids from Australian wastewater treatment plants.
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Crystal structure of the Helicobacter pylori enoyl-acyl carrier protein reductase in complex with hydroxydiphenyl ether compounds, triclosan and diclosan.
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Interaction of triclosan with eukaryotic membrane lipids.
  Eur J Oral Sci, 111, 216-222.  
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Targeting tuberculosis and malaria through inhibition of Enoyl reductase: compound activity and structural data.
  J Biol Chem, 278, 20851-20859.
PDB codes: 1p44 1p45
12499205 R.F.Waller, S.A.Ralph, M.B.Reed, V.Su, J.D.Douglas, D.E.Minnikin, A.F.Cowman, G.S.Besra, and G.I.McFadden (2003).
A type II pathway for fatty acid biosynthesis presents drug targets in Plasmodium falciparum.
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12832774 S.P.Muench, J.B.Rafferty, R.McLeod, D.W.Rice, and S.T.Prigge (2003).
Expression, purification and crystallization of the Plasmodium falciparum enoyl reductase.
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12000625 D.J.Stickler (2002).
Susceptibility of antibiotic-resistant Gram-negative bacteria to biocides: a perspective from the study of catheter biofilms.
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12037321 H.H.Lee, J.Yun, J.Moon, B.W.Han, B.I.Lee, J.Y.Lee, and S.W.Suh (2002).
Crystallization and preliminary X-ray crystallographic analysis of enoyl-acyl carrier protein reductase from Helicobacter pylori.
  Acta Crystallogr D Biol Crystallogr, 58, 1071-1073.  
12000613 K.Poole (2002).
Mechanisms of bacterial biocide and antibiotic resistance.
  J Appl Microbiol, 92, 55S-64S.  
11835284 N.Surolia, S.P.RamachandraRao, and A.Surolia (2002).
Paradigm shifts in malaria parasite biochemistry and anti-malarial chemotherapy.
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12573040 P.Gilbert, and A.J.McBain (2002).
Literature-based evaluation of the potential risks associated with impregnation of medical devices and implants with triclosan.
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12000619 P.Gilbert, D.G.Allison, and A.J.McBain (2002).
Biofilms in vitro and in vivo: do singular mechanisms imply cross-resistance?
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11959554 Q.Li, J.Y.Lee, R.Castillo, M.S.Hixon, C.Pujol, V.R.Doppalapudi, H.M.Shepard, G.M.Wahl, T.J.Lobl, and M.F.Chan (2002).
NB2001, a novel antibacterial agent with broad-spectrum activity and enhanced potency against beta-lactamase-producing strains.
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  11369293 D.J.Payne, P.V.Warren, D.J.Holmes, Y.Ji, and J.T.Lonsdale (2001).
Bacterial fatty-acid biosynthesis: a genomics-driven target for antibacterial drug discovery.
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11296236 D.M.van Aalten, C.C.DiRusso, and J.Knudsen (2001).
The structural basis of acyl coenzyme A-dependent regulation of the transcription factor FadR.
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PDB codes: 1h9g 1h9t
11180655 E.B.Martin, L.P.Mansfield, A.Smith, and S.J.Forsythe (2001).
Inhibition of light emission from the bioluminescent bacterium Vibrio fischeri after exposure to triclosan and related hygiene care products.
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11544358 J.W.Campbell, and J.E.Cronan (2001).
Bacterial fatty acid biosynthesis: targets for antibacterial drug discovery.
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11682176 M.J.Meade, R.L.Waddell, and T.M.Callahan (2001).
Soil bacteria Pseudomonas putida and Alcaligenes xylosoxidans subsp. denitrificans inactivate triclosan in liquid and solid substrates.
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Lipid biosynthesis as a target for antibacterial agents.
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Tuberculin skin testing in the era of multidrug-resistant tuberculosis.
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PDB code: 1edo
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Results of two observational studies in eight medical-surgical intensive care units in Germany to determine the frequency of hand washing by the medical staff and plot these results against the patient:personnel ratio
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11069675 R.A.Slayden, R.E.Lee, and C.E.Barry (2000).
Isoniazid affects multiple components of the type II fatty acid synthase system of Mycobacterium tuberculosis.
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Inhibition of the Staphylococcus aureus NADPH-dependent enoyl-acyl carrier protein reductase by triclosan and hexachlorophene.
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10823558 S.E.Brooks, M.A.Walczak, and H.Rizwanullah (2000).
Are we doing enough to contain Acinetobacter infections?
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Inhibition of InhA, the enoyl reductase from Mycobacterium tuberculosis, by triclosan and isoniazid.
  Biochemistry, 39, 7645-7650.  
10823560 T.Eckmanns, A.Rath, H.Rüden, P.Gastmeier, and F.Daschner (2000).
Outbreak of Enterobacter cloacae related to understaffing, overcrowding, and poor hygiene practices.
  Infect Control Hosp Epidemiol, 21, 305.  
10521472 A.Roujeinikova, S.Sedelnikova, G.J.de Boer, A.R.Stuitje, A.R.Slabas, J.B.Rafferty, and D.W.Rice (1999).
Inhibitor binding studies on enoyl reductase reveal conformational changes related to substrate recognition.
  J Biol Chem, 274, 30811-30817.
PDB code: 1cwu
  10419969 M.N.Alekshun, and S.B.Levy (1999).
Alteration of the repressor activity of MarR, the negative regulator of the Escherichia coli marRAB locus, by multiple chemicals in vitro.
  J Bacteriol, 181, 4669-4672.  
  10464225 T.T.Hoang, and H.P.Schweizer (1999).
Characterization of Pseudomonas aeruginosa enoyl-acyl carrier protein reductase (FabI): a target for the antimicrobial triclosan and its role in acylated homoserine lactone synthesis.
  J Bacteriol, 181, 5489-5497.  
  10595560 X.Qiu, C.A.Janson, R.I.Court, M.G.Smyth, D.J.Payne, and S.S.Abdel-Meguid (1999).
Molecular basis for triclosan activity involves a flipping loop in the active site.
  Protein Sci, 8, 2529-2532.
PDB code: 1c14
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.