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Nat Protoc. 2010 Dec;5(12):1967-73. doi: 10.1038/nprot.2010.164. Epub 2010 Nov 18.

A concise and scalable route to L-azidohomoalanine.

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  • 1School of Chemistry, Centre for Biomolecular Sciences, University of Nottingham, University Park, Nottingham, UK.


A concise and highly efficient synthetic route to L-azidohomoalanine (L-Aha) and its homologues is presented here. These chemically modified amino acids are used for the introduction of bioorthogonal handles into proteins. The described route avoids major problems of previously reported methods including expensive starting materials, low efficiency, and lack of scalability. Starting from inexpensive N-Boc-O-Bn-L-aspartic acid, gram quantities of L-Aha hydrochloride can be prepared with high purity. The reactions can be completed within 1 week and the products can be incorporated into proteins using L-methionine auxotrophs.

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