Enantioselective synthesis of cyanohydrins catalysed by hydroxynitrile lyases - a review

Org Biomol Chem. 2016 Jul 6;14(27):6375-89. doi: 10.1039/c6ob00934d.

Abstract

The first enantioselective synthesis was the selective addition of cyanide to benzaldehyde catalysed by a hydroxynitrile lyase (HNL). Since then these enzymes have been developed into a reliable tool in organic synthesis. HNLs to prepare either the (R)- or the (S)-enantiomer of the desired cyanohydrin are available and a wide variety of reaction conditions can be applied. As a result of this, numerous applications of these enzymes in organic synthesis have been described. Here the examples of the last decade are summarised, the enzyme catalysed step is discussed and the follow-up chemistry is shown. This proves HNLs to be part of main stream organic synthesis. Additionally the newest approaches via immobilisation and reaction engineering are introduced.

Publication types

  • Review

MeSH terms

  • Aldehyde-Lyases / chemistry
  • Aldehyde-Lyases / metabolism*
  • Chemistry Techniques, Synthetic
  • Enzymes, Immobilized / chemistry
  • Enzymes, Immobilized / metabolism
  • Nitriles / chemical synthesis*
  • Nitriles / chemistry*
  • Stereoisomerism
  • Substrate Specificity

Substances

  • Enzymes, Immobilized
  • Nitriles
  • cyanohydrin
  • Aldehyde-Lyases
  • mandelonitrile lyase