Metabolic perturbation of an essential pathway: evaluation of a glycine precursor of coenzyme A

J Am Chem Soc. 2013 Apr 24;135(16):5962-5. doi: 10.1021/ja400795m. Epub 2013 Apr 10.

Abstract

Pantetheine and its corresponding disulfide pantethine play a key role in metabolism as building blocks of coenzyme A (CoA), an essential cofactor utilized in ~4% of primary metabolism and central to fatty acid, polyketide, and nonribosomal peptide synthases. Using a combination of recombinant engineering and chemical synthesis, we show that the disulfide of N-pantoylglycyl-2-aminoethanethiol (GlyPan), with one fewer carbon than pantetheine, can rescue a mutant E. coli strain MG1655ΔpanC lacking a functional pantothenate synthetase. Using mass spectrometry, we show that the GlyPan variant is accepted by the downstream CoA biosynthetic machinery, ultimately being incorporated into essential acyl carrier proteins. These findings point to further flexibility in CoA-dependent pathways and offer the opportunity to incorporate orthogonal analogues.

Publication types

  • Research Support, N.I.H., Extramural

MeSH terms

  • Acyl Carrier Protein / metabolism
  • Amino Acid Sequence
  • Chromatography, High Pressure Liquid
  • Coenzyme A / biosynthesis
  • Coenzyme A / metabolism*
  • Disulfides
  • Electrophoresis, Polyacrylamide Gel
  • Escherichia coli / drug effects
  • Escherichia coli / genetics
  • Escherichia coli / metabolism
  • Glycine / metabolism*
  • Mass Spectrometry
  • Metabolic Networks and Pathways
  • Molecular Sequence Data
  • Pantetheine / analogs & derivatives
  • Pantetheine / metabolism
  • Peptide Synthases / genetics
  • Peptide Synthases / metabolism
  • Phosphotransferases (Alcohol Group Acceptor) / metabolism
  • Urea / chemistry

Substances

  • Acyl Carrier Protein
  • Disulfides
  • Pantetheine
  • pantethine
  • Urea
  • Phosphotransferases (Alcohol Group Acceptor)
  • pantothenate kinase
  • Peptide Synthases
  • pantothenate synthetase
  • Coenzyme A
  • Glycine