Stereochemistry of enzymatic water addition to C=C bonds

Biotechnol Adv. 2015 Sep-Oct;33(5):526-46. doi: 10.1016/j.biotechadv.2015.01.007. Epub 2015 Jan 30.

Abstract

Water addition to carbon-carbon double bonds using hydratases is attracting great interest in biochemistry. Most of the known hydratases are involved in primary metabolism and to a lesser extent in secondary metabolism. New hydratases have recently been added to the toolbox, both from natural sources or artificial metalloenzymes. In order to comprehensively understand how the hydratases are able to catalyse the water addition to carbon-carbon double bonds, this review will highlight the mechanistic and stereochemical studies of the enzymatic water addition to carbon-carbon double bonds, focusing on the syn/anti-addition and stereochemistry of the reaction.

Keywords: Alcohol; Anti-addition; Hydratase; Hydro-lyase; Michael addition; Stereochemistry; Syn-addition; Water addition.

Publication types

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

MeSH terms

  • Biochemistry
  • Carbon
  • Catalysis
  • Hydro-Lyases / metabolism*
  • Stereoisomerism
  • Water / chemistry*
  • Water / metabolism*

Substances

  • Water
  • Carbon
  • Hydro-Lyases