Identification of the two essential groups in the family 3 beta-glucosidase from Flavobacterium meningosepticum by labelling and tandem mass spectrometric analysis

Biochem J. 2002 Aug 1;365(Pt 3):857-63. doi: 10.1042/BJ20020186.

Abstract

beta-Glucosidase from Flavobacterium meningosepticum (Fbgl) catalyses the hydrolysis of beta-1,4-glucosidic bonds via a two-step double-displacement mechanism in which two amino acid residues act as nucleophile and acid/base catalyst. Definitive identification of these two residues is provided by the two active-site-directed inactivators, 2',4'-dinitrophenyl-2-deoxy-2-fluoro-beta-d-glucoside (2FDNPG) and N-bromoacetyl-beta-d-glucosylamine (NBGN), which stoichiometrically label the nucleophile and the acid/base catalyst of Fbgl, respectively. Pseudo-first-order inactivation rate constants (k(i)) of 0.25+/-0.01 and 0.05+/-0.01 min(-1) and dissociation constants (K(i)) of 90+/-15 and 4.4+/-0.2 mM are determined for 2FDNPG and NBGN, respectively. Proteolytic digestion of the labelled proteins, followed by peptide mapping and tandem MS analysis identify Asp-247 and Glu-473 as the catalytic nucleophile and acid/base residues, respectively, of Fbgl. This study confirms that the catalytic nucleophile of family 3 glycohydrolase is conserved across sub-families. However, different sub-families may have unique general acid/base catalysts.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Acetylglucosamine / analogs & derivatives*
  • Acetylglucosamine / metabolism*
  • Amino Acid Sequence
  • Binding Sites
  • Flavobacterium / chemistry
  • Flavobacterium / enzymology*
  • Glucosides / chemistry*
  • Mass Spectrometry
  • Molecular Sequence Data
  • Molecular Structure
  • Peptides / metabolism
  • beta-Glucosidase / chemistry
  • beta-Glucosidase / genetics
  • beta-Glucosidase / metabolism*

Substances

  • Glucosides
  • Peptides
  • N-bromoacetylglucosamine
  • beta-Glucosidase
  • Acetylglucosamine