An unexpected promiscuous activity of 4-oxalocrotonate tautomerase: the cis-trans isomerisation of nitrostyrene

Chembiochem. 2012 Sep 3;13(13):1869-73. doi: 10.1002/cbic.201200371. Epub 2012 Jul 31.

Abstract

Serendipitous switch: While exploring cis-nitrostyrene as a potential electrophile in Michael-type addition reactions catalysed by the enzyme 4-oxalocrotonate tautomerase (4-OT), it was unexpectedly found that 4-OT catalyses the isomerisation of cis-nitrostyrene to trans-nitrostyrene (k(cat) /K(m) = 1.9×10(3) M(-1) s(-1) ).

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Isomerases / metabolism*
  • Isomerism
  • Kinetics
  • Models, Molecular
  • Pseudomonas putida / chemistry
  • Pseudomonas putida / enzymology*
  • Pseudomonas putida / metabolism
  • Styrenes / chemistry
  • Styrenes / metabolism*
  • Substrate Specificity

Substances

  • Styrenes
  • beta-nitrostyrene
  • 4-oxalocrotonate tautomerase
  • Isomerases