Structure of a class III engineered cephalosporin acylase: comparisons with class I acylase and implications for differences in substrate specificity and catalytic activity

Biochem J. 2013 Apr 15;451(2):217-26. doi: 10.1042/BJ20121715.

Abstract

The crystal structure of the wild-type form of glutaryl-7-ACA (7-aminocephalosporanic acid) acylase from Pseudomonas N176 and a double mutant of the protein (H57βS/H70βS) that displays enhanced catalytic efficiency on cephalosporin C over glutaryl-7-aminocephalosporanic acid has been determined. The structures show a heterodimer made up of an α-chain (229 residues) and a β-chain (543 residues) with a deep cavity, which constitutes the active site. Comparison of the wild-type and mutant structures provides insights into the molecular reasons for the observed enhanced specificity on cephalosporin C over glutaryl-7-aminocephalosporanic acid and offers the basis to evolve a further improved enzyme variant. The nucleophilic catalytic serine residue, Ser(1β), is situated at the base of the active site cavity. The electron density reveals a ligand covalently bound to the catalytic serine residue, such that a tetrahedral adduct is formed. This is proposed to mimic the transition state of the enzyme for both the maturation step and the catalysis of the substrates. A view of the transition state configuration of the enzyme provides important insights into the mechanism of substrate binding and catalysis.

Publication types

  • Comparative Study
  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amidohydrolases / chemistry
  • Amidohydrolases / metabolism
  • Catalysis
  • Catalytic Domain
  • Cephalosporins / metabolism
  • Crystallography, X-Ray
  • Kinetics
  • Mutation
  • Penicillin Amidase / chemistry*
  • Penicillin Amidase / genetics
  • Penicillin Amidase / metabolism*
  • Protein Conformation
  • Pseudomonas / enzymology
  • Recombinant Proteins / chemistry
  • Recombinant Proteins / genetics
  • Recombinant Proteins / metabolism
  • Serine / metabolism
  • Substrate Specificity

Substances

  • Cephalosporins
  • Recombinant Proteins
  • cephalosporin C
  • Serine
  • 7-aminocephalosporanic acid
  • Amidohydrolases
  • Penicillin Amidase
  • aminoacylase I

Associated data

  • PDB/4HSR
  • PDB/4HST