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

Product Name Fmoc - Azidohomoalanine
CAS 942518-20-9
Size 100 mg
Catalog # 63670
US$ $423
Purity ≥95% by HPLC
Description

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

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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 366.3
Molecular Formula C19H18N4O4
     
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