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

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

doi:10.1038/nprot.2007.268

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

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

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33 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 language	English (US)
Pages (from-to)	1879-1883
Number of pages	5
Journal	Nature Protocols
Volume	2
Issue number	8
DOIs	https://doi.org/10.1038/nprot.2007.268
State	Published - Aug 2007

All Science Journal Classification (ASJC) codes

Biochemistry, Genetics and Molecular Biology(all)

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10.1038/nprot.2007.268

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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.",

author = "Link, {A. James} and Vink, {Mandy K.S.} and Tirrell, {David A.}",

note = "Funding Information: ACKNOWLEDGMENTS We thank Rebecca Connor and Nick Fisk for refinements to this protocol. This work was supported by NIH, by an NSF graduate fellowship to A.J.L. and by a grant from the Netherlands Organization for Scientific Research to M.K.S.V.",

year = "2007",

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AU - Tirrell, David A.

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AB - 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.

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

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