Identification of potential active-site residues in the hydroxynitrile lyase from Manihot esculenta by site-directed mutagenesis

J Biol Chem. 1996 Oct 18;271(42):25830-4. doi: 10.1074/jbc.271.42.25830.

Abstract

The hydroxynitrile lyase from cassava (Manihot esculenta Crantz) (EC 4.1.2.37) catalyzes the decomposition of the achiral alpha-hydroxynitrile acetone cyanohydrin into HCN and acetone during cyanogenesis of damaged plants. This enzyme can also be used for stereoselective synthesis of a wide array of (S)-cyanohydrins by addition of HCN to aldehydes or ketones. Optically active cyanohydrins are interesting intermediates for the synthesis of alpha-hydroxy acids, alpha-hydroxy ketones, or beta-ethanolamines, all of which are important building blocks in organic synthesis. Inhibition of hydroxynitrile lyase from M. esculenta (MeHNL) by serine- and histidine-modifying reagents suggests involvement of active site seryl and histidyl residues. Furthermore, serine 80 of MeHNL is part of the active site motif Gly-X-Ser-X-Gly/Ala, often considered as the hallmark of catalytic triads having independently evolved in four groups of enzymes: the alpha/beta hydrolase fold enzymes, subtilisins, the cysteine proteases, and the eukaryotic serine proteases. By site-directed mutagenesis, three residues critical for enzyme activity have been identified: serine 80, aspartic acid 208, and histidine 236. These residues may be directly involved in MeHNL-catalyzed decomposition of cyanohydrins, providing evidence for a catalytical triad in HNLs, too. The order of the catalytic triad residues in the primary sequence of MeHNL is nucleophile-histidine-acid, suggesting that MeHNL belongs to the alpha/beta hydrolase fold group of enzymes. In contrast to all other enzymes having a catalytical triad, HNLs catalyze no net hydrolytic reactions.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Aldehyde-Lyases / genetics
  • Aldehyde-Lyases / metabolism*
  • Amino Acid Sequence
  • Aspartic Acid
  • Base Sequence
  • Binding Sites
  • Electrophoresis, Polyacrylamide Gel
  • Histidine
  • Manihot
  • Molecular Sequence Data
  • Mutagenesis, Site-Directed
  • Nitriles / metabolism
  • Sequence Alignment
  • Serine / metabolism

Substances

  • Nitriles
  • Aspartic Acid
  • Serine
  • Histidine
  • acetone cyanohydrin
  • Aldehyde-Lyases
  • acetone-cyanohydrin lyase