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Nat Protoc. 2007;2(8):1879-83.

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

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1
Division of Chemistry and Chemical Engineering, California Institute of Technology, Pasadena, California 91106, USA. ajlink@princeton.edu

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.

PMID:
17703198
DOI:
10.1038/nprot.2007.268
[Indexed for MEDLINE]
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