Structure function analysis of benzalacetone synthase from Rheum palmatum

Bioorg Med Chem Lett. 2007 Jun 1;17(11):3161-6. doi: 10.1016/j.bmcl.2007.03.029. Epub 2007 Mar 15.

Abstract

Benzalacetone synthase (BAS) is a plant-specific chalcone synthase (CHS) superfamily type III polyketide synthase (PKS) that catalyzes a one-step decarboxylative condensation of 4-coumaroyl-CoA with malonyl-CoA. The diketide forming activity of Rheum palmatum BAS is attributed to the characteristic substitution of the conserved active-site Phe215 with Leu (numbering in Medicago sativa CHS). To further understand the structure and function of R. palmatum BAS, four site-directed mutants (C197T, C197G, G256L, and S338V) were newly constructed. All the mutants did not change the product pattern, however, the activity was 2-fold increased in S338V, while reduced to half in G256L mutant. On the other hand, the C197 mutants were functionally almost identical to wild-type BAS, excluding the possibility that the second active-site Cys is involved in the enzyme reaction. Instead, homology modeling suggested a possibility that, unlike the case of CHS, BAS utilizes an alternative pocket to lock the coumaroyl moiety for the diketide formation reaction.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Acyl Coenzyme A / chemistry
  • Acyltransferases / chemistry*
  • Acyltransferases / genetics
  • Acyltransferases / isolation & purification
  • Amino Acid Sequence
  • Amino Acid Substitution
  • Binding Sites
  • Butanones / metabolism*
  • Hydrogen-Ion Concentration
  • Malonyl Coenzyme A / chemistry
  • Molecular Sequence Data
  • Mutagenesis, Site-Directed
  • Mutation
  • Protein Conformation
  • Rheum / enzymology*
  • Substrate Specificity

Substances

  • Acyl Coenzyme A
  • Butanones
  • 4-coumaroyl-coenzyme A
  • Malonyl Coenzyme A
  • benzylideneacetone
  • Acyltransferases
  • flavanone synthetase