title: Preparation of the functionalizable methionine surrogate azidohomoalanine via copper-catalyzed diazo transfer.
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.
authors: Division of Chemistry and Chemical Engineering, California Institute of Technology, Pasadena, California 91106, USA. ajlink@princeton.edu
authors: A James
authors: AJ
authors: Link
authors: Mandy K S
authors: MK
authors: Vink
authors: David A
authors: DA
authors: Tirrell
mesh_terms: D000409:Alanine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000302:isolation & purification; D001671:Biochemistry / Q000379:methods; D002087:Butyrates / Q000737:chemistry; D002384:Catalysis; D002852:Chromatography, Ion Exchange; D003300:Copper / Q000737:chemistry*; D003460:Crystallization; D005663:Furans / Q000737:chemistry; D008715:Methionine / Q000737:chemistry; D013449:Sulfonamides / Q000737:chemistry
chemical_list: D002087:Butyrates; D005663:Furans; D013449:Sulfonamides; C506098:azidohomoalanine; D003300:Copper; C474725:triflic anhydride; D008715:Methionine; D000409:Alanine