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Amino Acids  >  Unusual Amino Acids  >  Azide and Alkyne containing Amino Acids  >>  Azidohomoalanine

Product Name Azidohomoalanine
Size 100 mg
Catalog # AS-63669
US$ $545
Purity One spot by TLC

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

Detailed Information Material Safety Data Sheets (MSDS)
Storage -20░C Protected from Light
References 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.
Molecular Weight 144.1
Molecular Formula C4H8N4O2
Product Citations Eichelbaum, K. and K. Jeroen. (2014). Combining pulsed SILAC labeling and click-chemistry for quantitative secretome analysis. Exocytosis and Endocytosis. Springer New York, 101.

Francis, SP. et al. (2013). A novel role of cytosolic protein synthesis inhibition in aminoglycoside ototoxicity. J Neurosci 33, 3079.

Yang, F. et al. (2013). Doxorubicin enhances nucleosome turnover around promoters. Curr Biol 23 782.

Zhang, H.et al. (2013). Bio-inspired liposomal thrombomodulin conjugate through bio-orthogonal chemistry. Bioconjugate Chem 24, 550.

Eger, S. et al. (2012). Formation of Ubiquitin dimers via AzideľAlkyne click reaction. Ubiquitin Family Modifiers and the Proteasome. Humana Press. 589.

Deal, R. et al. (2010). Genome-Wide Kinetics of Nucleosome Turnover Determined by Metabolic Labeling of Histones. Science 328, 1161.
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