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Synlett 2011(13): 1917-1919  
DOI: 10.1055/s-0030-1260950
LETTER
© Georg Thieme Verlag Stuttgart ˙ New York

Efficient Synthesis of Fmoc-Protected Azido Amino Acids

Yu Heng Lau, David R. Spring*
Department of Chemistry, University of Cambridge, Lensfield Rd, Cambridge, CB2 1EW, UK
Fax: +44(1223)336362; e-Mail: spring@ch.cam.ac.uk;
Further Information

Publication History

Received 15 April 2011
Publication Date:
14 July 2011 (online)

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Abstract

The efficient two-step synthesis of Fmoc-protected l-azidoalanine and l-azidohomoalanine from readily available Fmoc-protected asparagine and glutamine, respectively, is reported. The synthetic route proceeds in good yield, requires no extra purification steps, and can be carried out on gram scale. The resulting azido amino acids are of sufficient purity for solid-phase peptide synthesis, as demonstrated in the synthesis of a model pentapeptide.

Key words

azides - amino acids - diazo transfer - Hofmann rearrangement - Fmoc solid-phase peptide synthesis

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