Structural and kinetic characterization of 4-hydroxy-4-methyl-2-oxoglutarate/4-carboxy-4-hydroxy-2-oxoadipate aldolase, a protocatechuate degradation enzyme evolutionarily convergent with the HpaI and DmpG pyruvate aldolases

J Biol Chem. 2010 Nov 19;285(47):36608-15. doi: 10.1074/jbc.M110.159509. Epub 2010 Sep 15.

Abstract

4-Hydroxy-4-methyl-2-oxoglutarate/4-carboxy-4-hydroxy-2-oxoadipate (HMG/CHA) aldolase from Pseudomonas putida F1 catalyzes the last step of the bacterial protocatechuate 4,5-cleavage pathway. The preferred substrates of the enzyme are 2-keto-4-hydroxy acids with a 4-carboxylate substitution. The enzyme also exhibits oxaloacetate decarboxylation and pyruvate α-proton exchange activity. Sodium oxalate is a competitive inhibitor of the aldolase reaction. The pH dependence of k(cat)/K(m) and k(cat) for the enzyme is consistent with a single deprotonation with pK(a) values of 8.0 ± 0.1 and 7.0 ± 0.1 for free enzyme and enzyme substrate complex, respectively. The 1.8 Å x-ray structure shows a four-layered α-β-β-α sandwich structure with the active site at the interface of two adjacent subunits of a hexamer; this fold resembles the RNase E inhibitor, RraA, but is novel for an aldolase. The catalytic site contains a magnesium ion ligated by Asp-124 as well as three water molecules bound by Asp-102 and Glu-199'. A pyruvate molecule binds the magnesium ion through both carboxylate and keto oxygen atoms, completing the octahedral geometry. The carbonyl oxygen also forms hydrogen bonds with the guanadinium group of Arg-123, which site-directed mutagenesis confirms is essential for catalysis. A mechanism for HMG/CHA aldolase is proposed on the basis of the structure, kinetics, and previously established features of other aldolase mechanisms.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Aldehyde-Lyases / chemistry*
  • Aldehyde-Lyases / genetics
  • Aldehyde-Lyases / metabolism*
  • Crystallization
  • Crystallography, X-Ray
  • Evolution, Molecular*
  • Hydroxybenzoates / metabolism*
  • Kinetics
  • Oxaloacetic Acid / metabolism
  • Oxo-Acid-Lyases / chemistry*
  • Oxo-Acid-Lyases / genetics
  • Oxo-Acid-Lyases / metabolism*
  • Pseudomonas putida / enzymology*
  • Pyruvates / metabolism
  • Substrate Specificity

Substances

  • Hydroxybenzoates
  • Pyruvates
  • Oxaloacetic Acid
  • protocatechuic acid
  • 4-carboxy-4-hydroxy-2-oxoadipate aldolase
  • Aldehyde-Lyases
  • Oxo-Acid-Lyases
  • 4-hydroxy-4-methyl-2-oxoglutarate aldolase

Associated data

  • PDB/3NOJ