Roles of His291-alpha and His146-beta' in the reductive acylation reaction catalyzed by human branched-chain alpha-ketoacid dehydrogenase: refined phosphorylation loop structure in the active site

J Biol Chem. 2003 Oct 31;278(44):43402-10. doi: 10.1074/jbc.M306204200. Epub 2003 Aug 5.

Abstract

We report here that alterations of either His291-alpha or His146-beta' in the active site of human branched-chain alpha-ketoacid dehydrogenase (E1b) impede both the decarboxylation and the reductive acylation reactions catalyzed by E1b as well as the binding of cofactor thiamin diphosphate (ThDP). In a refined human E1b active-site structure, His291-alpha, which aligns with His407 in Escherichia coli pyruvate dehydrogenase and His263 in yeast transketolase, is on a largely ordered phosphorylation loop. The imidazole ring of His291-alpha in E1b coordinates to the terminal phosphate oxygen atoms of bound ThDP. The N3 atom of wild-type His146-beta', which can be protonated, binds a water molecule and points toward the aminopyrimidine ring of ThDP. Remarkably, the H291A-alpha mutation results in a complete order-to-disorder transition of the loop region, which precludes the binding of the substrate lipoyl-bearing domain to E1b. The H146A-beta' mutation, on the other hand, does not alter the loop structure, but nullifies the reductive acylation activity of E1b. Our results suggest that: 1) His291-alpha plays a structural rather than a catalytic role in the binding of cofactor ThDP and the lipoyl-bearing domain to E1b, and 2) His146-beta' is an essential catalytic residue, probably functioning as a proton donor in the reductive acylation of lipoamide on the lipoyl-bearing domain.

Publication types

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

MeSH terms

  • 3-Methyl-2-Oxobutanoate Dehydrogenase (Lipoamide) / chemistry*
  • 3-Methyl-2-Oxobutanoate Dehydrogenase (Lipoamide) / metabolism*
  • Amino Acid Sequence
  • Binding Sites
  • Calorimetry
  • Catalytic Domain
  • Dimerization
  • Histidine / chemistry*
  • Humans
  • Kinetics
  • Models, Chemical
  • Models, Molecular
  • Molecular Sequence Data
  • Mutation
  • Oxygen / chemistry
  • Oxygen / metabolism
  • Phosphorylation
  • Protein Binding
  • Protein Structure, Tertiary
  • Protons
  • Pyruvate Dehydrogenase Complex / metabolism
  • Sequence Homology, Amino Acid

Substances

  • Protons
  • Pyruvate Dehydrogenase Complex
  • Histidine
  • 3-Methyl-2-Oxobutanoate Dehydrogenase (Lipoamide)
  • Oxygen

Associated data

  • PDB/1OLS
  • PDB/1OLU
  • PDB/1OLX