A new type of peroxisomal acyl-coenzyme A synthetase from Arabidopsis thaliana has the catalytic capacity to activate biosynthetic precursors of jasmonic acid

J Biol Chem. 2005 Apr 8;280(14):13962-72. doi: 10.1074/jbc.M413578200. Epub 2005 Jan 26.

Abstract

Arabidopsis thaliana contains a large number of genes that encode carboxylic acid-activating enzymes, including nine long-chain fatty acyl-CoA synthetases, four 4-coumarate:CoA ligases (4CL), and 25 4CL-like proteins of unknown biochemical function. Because of their high structural and sequence similarity with bona fide 4CLs and their highly hydrophobic putative substrate-binding pockets, the 4CL-like proteins At4g05160 and At5g63380 were selected for detailed analysis. Following heterologous expression, the purified proteins were subjected to a large scale screen to identify their preferred in vitro substrates. This study uncovered a significant activity of At4g05160 with medium-chain fatty acids, medium-chain fatty acids carrying a phenyl substitution, long-chain fatty acids, as well as the jasmonic acid precursors 12-oxo-phytodienoic acid and 3-oxo-2-(2'-pentenyl)-cyclopentane-1-hexanoic acid. The closest homolog of At4g05160, namely At5g63380, showed high activity with long-chain fatty acids and 12-oxo-phytodienoic acid, the latter representing the most efficiently converted substrate. By using fluorescent-tagged variants, we demonstrated that both 4CL-like proteins are targeted to leaf peroxisomes. Collectively, these data demonstrate that At4g05160 and At5g63380 have the capacity to contribute to jasmonic acid biosynthesis by initiating the beta-oxidative chain shortening of its precursors.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Acetates / metabolism
  • Amino Acid Sequence
  • Arabidopsis / cytology
  • Arabidopsis / enzymology*
  • Arabidopsis / genetics
  • Arabidopsis Proteins / chemistry
  • Arabidopsis Proteins / classification
  • Arabidopsis Proteins / genetics
  • Arabidopsis Proteins / metabolism*
  • Coenzyme A Ligases / chemistry
  • Coenzyme A Ligases / classification
  • Coenzyme A Ligases / genetics
  • Coenzyme A Ligases / metabolism*
  • Cyclopentanes / metabolism*
  • Fatty Acids / chemistry
  • Fatty Acids / metabolism
  • Gene Expression Regulation, Plant
  • Isoenzymes / genetics
  • Isoenzymes / metabolism
  • Molecular Structure
  • Oxylipins
  • Peroxisomes / enzymology*
  • Phylogeny
  • Plant Growth Regulators / metabolism*
  • Plant Leaves / cytology
  • Plant Leaves / enzymology
  • Recombinant Fusion Proteins / genetics
  • Recombinant Fusion Proteins / metabolism
  • Sequence Alignment

Substances

  • Acetates
  • Arabidopsis Proteins
  • Cyclopentanes
  • Fatty Acids
  • Isoenzymes
  • Oxylipins
  • Plant Growth Regulators
  • Recombinant Fusion Proteins
  • jasmonic acid
  • methyl jasmonate
  • Coenzyme A Ligases
  • At4g05160 protein, Arabidopsis
  • At5g63380 protein, Arabidopsis