Structural basis for the recognition of peptide RJPXD33 by acyltransferases in lipid A biosynthesis

J Biol Chem. 2014 May 30;289(22):15527-35. doi: 10.1074/jbc.M114.564278. Epub 2014 Apr 16.

Abstract

UDP-N-acetylglucosamine acyltransferase (LpxA) and UDP-3-O-(acyl)-glucosamine acyltransferase (LpxD) constitute the essential, early acyltransferases of lipid A biosynthesis. Recently, an antimicrobial peptide inhibitor, RJPXD33, was identified with dual affinity for LpxA and LpxD. To gain a fundamental understanding of the molecular basis of inhibitor binding, we determined the crystal structure of LpxA from Escherichia coli in complex with RJPXD33 at 1.9 Å resolutions. Our results suggest that the peptide binds in a unique modality that mimics (R)-β-hydroxyacyl pantetheine binding to LpxA and displays how the peptide binds exclusive of the native substrate, acyl-acyl carrier protein. Acyltransferase binding studies with photo-labile RJPXD33 probes and truncations of RJPXD33 validated the structure and provided fundamental insights for future design of small molecule inhibitors. Overlay of the LpxA-RJPXD33 structure with E. coli LpxD identified a complementary peptide binding pocket within LpxD and serves as a model for further biochemical characterization of RJPXD33 binding to LpxD.

Keywords: Acyl Carrier Protein (ACP); Acyltransferase; Antimicrobial Peptide (AMP); Enzyme Inhibitor; Lipid A; Lipopolysaccharide (LPS); LpxA; Peptides; X-ray Crystallography.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, Non-U.S. Gov't
  • Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

  • Acyl Carrier Protein / metabolism
  • Acyltransferases / chemistry
  • Acyltransferases / metabolism*
  • Catalytic Domain
  • Crystallography, X-Ray
  • Escherichia coli / enzymology*
  • Escherichia coli Proteins / chemistry
  • Escherichia coli Proteins / metabolism*
  • Fatty Acid Synthase, Type II / metabolism
  • Lipid A / biosynthesis*
  • Models, Molecular
  • Pantetheine / metabolism
  • Peptides / chemistry
  • Peptides / metabolism*
  • Protein Binding / physiology
  • Protein Structure, Tertiary
  • Structure-Activity Relationship
  • Substrate Specificity

Substances

  • Acyl Carrier Protein
  • Escherichia coli Proteins
  • Lipid A
  • Peptides
  • acpP protein, E coli
  • Pantetheine
  • Acyltransferases
  • acyl-(acyl-carrier-protein)-UDP-N-acetylglucosamine acyltransferase
  • Fatty Acid Synthase, Type II

Associated data

  • PDB/8J09