Self-malonylation is an intrinsic property of a chemically synthesized type II polyketide synthase acyl carrier protein

Biochemistry. 2005 Nov 22;44(46):15414-21. doi: 10.1021/bi051499i.

Abstract

During polyketide biosynthesis, malonyl groups are transferred to the acyl carrier protein (ACP) component of the polyketide synthase (PKS), and it has been shown that a number of type II polyketide ACPs undergo rapid self-acylation from malonyl-CoA in the absence of a malonyl-CoA:holo-acyl carrier protein transacylase (MCAT). More recently, however, the observation of self-malonylation has been ascribed to contamination with Escherichia coli MCAT (FabD) rather than an intrinsic property of the ACP. The wild-type apo-ACP from the actinorhodin (act) PKS of Streptomyces coelicolor (synthetic apo-ACP) has therefore been synthesized using solid-state peptide methods and refolded using the GroEL/ES chaperone system from E. coli. Correct folding of the act ACP has been confirmed by circular dichroism (CD) and 1H NMR. Synthetic apo-ACP was phosphopantetheinylated to 100% by S. coelicolor holo-acyl carrier protein synthase (ACPS), and the resultant holo-ACP underwent self-malonylation in the presence of malonyl-CoA. No malonylation of negative controls was observed, confirming that the use of ACPS and GroEL/ES did not introduce contamination with E. coli MCAT. This result proves unequivocally that self-malonylation is an inherent activity of this PKS ACP in vitro.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Acyl Carrier Protein / chemical synthesis*
  • Acyl Carrier Protein / metabolism*
  • Acyl-Carrier Protein S-Malonyltransferase / metabolism
  • Apoproteins / chemical synthesis
  • Apoproteins / metabolism
  • Chromatography, High Pressure Liquid
  • Circular Dichroism
  • Electrophoresis, Polyacrylamide Gel
  • Malonates / metabolism*
  • Nuclear Magnetic Resonance, Biomolecular
  • Polyketide Synthases / metabolism*
  • Protein Folding
  • Spectrometry, Mass, Electrospray Ionization
  • Streptomyces coelicolor / enzymology

Substances

  • Acyl Carrier Protein
  • Apoproteins
  • Malonates
  • Polyketide Synthases
  • malonic acid
  • polyketide beta-ketoacylsynthase
  • Acyl-Carrier Protein S-Malonyltransferase