Further studies on the catalytic mechanism of human liver alpha-L-fucosidase

Biochim Biophys Acta. 1987 Mar 18;912(1):132-8. doi: 10.1016/0167-4838(87)90256-1.

Abstract

Radiolabeling of human liver alpha-L-fucosidase (alpha-L-fucoside fucohydrolase, EC 3.2.1.51) with [1-3H]conduritol C trans-epoxide revealed that there are four active sites per tetrameric enzyme complex. Solvent isotope effect experiments give evidence for a proton transfer at the rate-limiting step in catalysis. Transglycosylase activity was observed using methanol as an alternative glycone acceptor to produce methyl alpha-L-fucoside, suggesting that alpha-L-fucose is formed when water is the acceptor. Initial burst kinetics experiments suggest that a glycosyl-enzyme intermediate is formed, although the magnitude of the burst is not stoichiometric with the number of active sites. These data, along with previous results, suggest a general acid-general base catalytic mechanism involving double inversion of stereochemistry at C-1 of fucose, as well as the formation of either a covalent glycosyl-enzyme intermediate or a tight ion pair between a charged active-site residue and a hypothetical fucosyl oxocarbonium ion intermediate.

Publication types

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

MeSH terms

  • Affinity Labels
  • Binding Sites
  • Catalysis
  • Glycosylation
  • Humans
  • Hydrogen-Ion Concentration
  • Kinetics
  • Liver / enzymology*
  • Solvents
  • alpha-L-Fucosidase / isolation & purification
  • alpha-L-Fucosidase / metabolism*

Substances

  • Affinity Labels
  • Solvents
  • alpha-L-Fucosidase