Preparation of the functionalizable methionine surrogate azidohomoalanine via copper-catalyzed diazo transfer

Nat Protoc. 2007;2(8):1879-83. doi: 10.1038/nprot.2007.268.

Abstract

The azide functional group has assumed a prominent role in chemical biology efforts in recent years. Azides may be readily introduced into proteins upon replacement of methionine residues with the non-canonical amino acid azidohomoalanine (AHA). This protocol describes a synthetic route to AHA based on the copper-catalyzed conversion of amines to azides. An alternate protocol for the preparation of AHA is presented in a companion paper. The synthesis and purification of AHA via the route described herein can be completed in 3-4 days.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, Non-U.S. Gov't
  • Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

  • Alanine / analogs & derivatives*
  • Alanine / chemical synthesis
  • Alanine / isolation & purification
  • Biochemistry / methods
  • Butyrates / chemistry
  • Catalysis
  • Chromatography, Ion Exchange
  • Copper / chemistry*
  • Crystallization
  • Furans / chemistry
  • Methionine / chemistry
  • Sulfonamides / chemistry

Substances

  • Butyrates
  • Furans
  • Sulfonamides
  • azidohomoalanine
  • Copper
  • triflic anhydride
  • Methionine
  • Alanine