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

A. James Link, Mandy K.S. Vink, David A. Tirrell

Research output: Contribution to journalArticlepeer-review

32 Scopus citations

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.

Original languageEnglish (US)
Pages (from-to)1879-1883
Number of pages5
JournalNature Protocols
Volume2
Issue number8
DOIs
StatePublished - Aug 1 2007

All Science Journal Classification (ASJC) codes

  • Biochemistry, Genetics and Molecular Biology(all)

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