An unusual amino acid used in Solid Phase Peptide Synthesis (SPPS) for the synthesis of modifiable side-chain peptides and proteins.1 The side-chain azido (N3) group is stable in trifluoroacetic acid (TFA) and piperidine (Pip), two reagents commonly used in SPPS. The azido group can be readily converted to an amine on the solid phase or in solution via the Staudinger reduction.2 In addition, incorporation of azidohomoalanine into proteins has shown promise as an effective IR probe into local electrostatic environments of proteins.3
1. Vallee, M. R. J.; Majkut, P.; Wilkening, C. W.; Muller, G.; Hackenberger, C. P. R. Staudinger-Phosphonite Reactions for the Chemoselective Transformation of Azido-Containing Peptides and Proteins.Org. Lett. 2011 (13) 5440-5443. 2. Staudinger, H.; Meyer, J. UberneueorganischePhosphorverbindungen III. Phosphinmethylenederivative und Phosphinimine. Helvetica Chim. Acta.1919 (2) 635-646. 3. Oh, K.-I.; Lee, J.-H.; Joo, C.; Han, H.; Cho, M. β-Azidoalanine as an IR Probe: Application to Amyloid A β (16-22) Aggregation. J. Phys. Chem. B.2008 (112) 10352-10357.
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