6TBC

Crystal structure of S. aureus FabI in complex with NADPH and kalimantacin B


Experimental Data Snapshot

  • Method: X-RAY DIFFRACTION
  • Resolution: 2.55 Å
  • R-Value Free: 0.237 
  • R-Value Work: 0.190 
  • R-Value Observed: 0.193 

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Ligand Structure Quality Assessment 


This is version 1.4 of the entry. See complete history


Literature

The Kalimantacin Polyketide Antibiotics Inhibit Fatty Acid Biosynthesis in Staphylococcus aureus by Targeting the Enoyl-Acyl Carrier Protein Binding Site of FabI.

Fage, C.D.Lathouwers, T.Vanmeert, M.Gao, L.J.Vrancken, K.Lammens, E.M.Weir, A.N.M.Degroote, R.Cuppens, H.Kosol, S.Simpson, T.J.Crump, M.P.Willis, C.L.Herdewijn, P.Lescrinier, E.Lavigne, R.Anne, J.Masschelein, J.

(2020) Angew Chem Int Ed Engl 59: 10549-10556

  • DOI: https://doi.org/10.1002/anie.201915407
  • Primary Citation of Related Structures:  
    6TBB, 6TBC

  • PubMed Abstract: 

    The enoyl-acyl carrier protein reductase enzyme FabI is essential for fatty acid biosynthesis in Staphylococcus aureus and represents a promising target for the development of novel, urgently needed anti-staphylococcal agents. Here, we elucidate the mode of action of the kalimantacin antibiotics, a novel class of FabI inhibitors with clinically-relevant activity against multidrug-resistant S. aureus. By combining X-ray crystallography with molecular dynamics simulations, in vitro kinetic studies and chemical derivatization experiments, we characterize the interaction between the antibiotics and their target, and we demonstrate that the kalimantacins bind in a unique conformation that differs significantly from the binding mode of other known FabI inhibitors. We also investigate mechanisms of acquired resistance in S. aureus and identify key residues in FabI that stabilize the binding of the antibiotics. Our findings provide intriguing insights into the mode of action of a novel class of FabI inhibitors that will inspire future anti-staphylococcal drug development.


  • Organizational Affiliation

    Department of Chemistry, University of Warwick, Coventry, CV4 7AL, UK.


Macromolecules
Find similar proteins by:  (by identity cutoff)  |  3D Structure
Entity ID: 1
MoleculeChains Sequence LengthOrganismDetailsImage
Enoyl-[acyl-carrier-protein] reductase [NADPH]
A, B, C, D, E
A, B, C, D, E, F, G, H
261Staphylococcus aureusMutation(s): 0 
EC: 1.3.1.39
UniProt
Find proteins for Q6GI75 (Staphylococcus aureus (strain MRSA252))
Explore Q6GI75 
Go to UniProtKB:  Q6GI75
Entity Groups  
Sequence Clusters30% Identity50% Identity70% Identity90% Identity95% Identity100% Identity
UniProt GroupQ6GI75
Sequence Annotations
Expand
  • Reference Sequence
Small Molecules
Ligands 2 Unique
IDChains Name / Formula / InChI Key2D Diagram3D Interactions
NDP
Query on NDP

Download Ideal Coordinates CCD File 
I [auth A]
K [auth B]
M [auth C]
O [auth D]
Q [auth E]
I [auth A],
K [auth B],
M [auth C],
O [auth D],
Q [auth E],
S [auth F],
U [auth G],
W [auth H]
NADPH DIHYDRO-NICOTINAMIDE-ADENINE-DINUCLEOTIDE PHOSPHATE
C21 H30 N7 O17 P3
ACFIXJIJDZMPPO-NNYOXOHSSA-N
N5H (Subject of Investigation/LOI)
Query on N5H

Download Ideal Coordinates CCD File 
J [auth A]
L [auth B]
N [auth C]
P [auth D]
R [auth E]
J [auth A],
L [auth B],
N [auth C],
P [auth D],
R [auth E],
T [auth F],
V [auth G],
X [auth H]
(2~{E},5~{R},10~{E},12~{E},15~{S},19~{R})-20-[[(2~{R},3~{R})-3-aminocarbonyloxy-2-methyl-butanoyl]amino]-3,5,15-trimethyl-7-methylidene-19-oxidanyl-17-oxidanylidene-icosa-2,10,12-trienoic acid
C30 H48 N2 O7
GENAAYFYLGYPIQ-YPMJEBJESA-N
Experimental Data & Validation

Experimental Data

  • Method: X-RAY DIFFRACTION
  • Resolution: 2.55 Å
  • R-Value Free: 0.237 
  • R-Value Work: 0.190 
  • R-Value Observed: 0.193 
  • Space Group: P 21 21 21
Unit Cell:
Length ( Å )Angle ( ˚ )
a = 64.316α = 90
b = 108.564β = 90
c = 296.183γ = 90
Software Package:
Software NamePurpose
XDSdata reduction
Aimlessdata scaling
PHASERphasing
REFMACrefinement
PDB_EXTRACTdata extraction

Structure Validation

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Ligand Structure Quality Assessment 


Entry History & Funding Information

Deposition Data


Funding OrganizationLocationGrant Number
Research Foundation - FlandersBelgium12H1716N
Engineering and Physical Sciences Research CouncilUnited KingdomEP/M027503/1

Revision History  (Full details and data files)

  • Version 1.0: 2020-04-01
    Type: Initial release
  • Version 1.1: 2020-04-08
    Changes: Database references
  • Version 1.2: 2020-07-01
    Changes: Database references
  • Version 1.3: 2020-10-21
    Changes: Structure summary
  • Version 1.4: 2024-01-24
    Changes: Advisory, Data collection, Database references, Refinement description