An enzymatic route to selenazolines

Chembiochem. 2013 Mar 18;14(5):564-7. doi: 10.1002/cbic.201300037. Epub 2013 Feb 18.

Abstract

Ringing the changes: Selenazolines have applications in medicinal chemistry, but their synthesis is challenging. We report a new convenient and less toxic route to these heterocycles that starts from commercially available selenocysteine. The new route depends on a heterocyclase enzyme that creates oxazolines and thiazolines from serines/threonines and cysteines.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amino Acid Sequence
  • Cysteine / chemistry
  • Cysteine / metabolism
  • Iodoacetamide / chemistry
  • Multienzyme Complexes / metabolism*
  • Oxazoles / chemistry
  • Oxazoles / metabolism
  • Peptides, Cyclic / biosynthesis
  • Peptides, Cyclic / chemistry
  • Selenium / chemistry*
  • Selenium / metabolism
  • Selenocysteine / chemistry
  • Selenocysteine / metabolism
  • Serine / chemistry
  • Serine / metabolism
  • Spectrometry, Mass, Matrix-Assisted Laser Desorption-Ionization
  • Thiazoles / chemistry
  • Thiazoles / metabolism
  • Threonine / chemistry
  • Threonine / metabolism

Substances

  • Multienzyme Complexes
  • Oxazoles
  • Peptides, Cyclic
  • Thiazoles
  • Selenocysteine
  • patellamide D
  • Threonine
  • Serine
  • Selenium
  • Cysteine
  • Iodoacetamide