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H-L-Tyr(2-azidoethyl)-OH
Chemical name: O-2-azidoethyl-tyrosine // Synonyms: H-Tyr(2-azidoethyl)-OH, (S)-2-amino-3-(4-(2-azidoethoxy)phenyl)propanoic acid, Azidoethoxyphenylalanine, AePhe, H-L-Phe(4-(2-azidoethoxy))-OH,(2S)-2-amino-3-[4-(2-azidoethoxy)phenyl]propanoic acid, H-Phe(4-(2-azidoethoxy))-OH, p2AzY, 4-(2-azidoetho
- Product code:HAA9310
- CAS No.:1570523-47-5
- Formula:C11H14N4O3
- Storage temperature:2-8°C
- Molecular weight:250.26 g/mol
- Purity :min. 98%
- Enantiomeric Purity:min. 99,7%
from $150.00
description
This unnatural Tyrosine derivative bears an azidoethyl substitution as reactive handle e.g. for biorthogonal conjugations, via a Cu(I)-catalyzed 1,3-dipolar Click cycloaddition with alkynes. Furthermore, this NCAA can be incorporated into proteins and used as an IR vibrational reporter and Click-chemistry partner.
This product is also available as HCl salt. Fore product details see HAA9215.
references
The genetic incorporation of thirteen novel non-canonical amino acids; A. Tuley, Y.-S. Wang, X. Fang, Y. Kurra, Y. H. Rezenom, W. R. Liu; Chem. Commun. 2014; 50: 2673-2675. https://doi.org/10.1039/C3CC49068H
Azidoethoxyphenylalanine as a Vibrational Reporter and Click Chemistry Partner in Proteins; E. M. Tookmanian, C. M. Phillips-Piro, E. E. Fenlon, S. H. Brewer; Chem. Eur. J. 2015; 21(52): 19096-19103. https://doi.org/10.1002/chem.201503908
Synthesis and Incorporation of Unnatural Amino Acids To Probe and Optimize Protein Bioconjugations; J. C. Maza, J. R. McKenna, B. K. Raliski, M. T. Freedman, D. D. Young; Bioconjugate Chem. 2015; 26(9): 1884-1889. https://doi.org/10.1021/acs.bioconjchem.5b00424
Side-chain-to-tail cyclization of ribosomally derived peptides promoted by aryl and alkyl amino-functionalized unnatural amino acids; J. R. Frost, Z. Wu, Y. C. Lam, A. E. Owens, R. Fasan; Org. Biomol. Chem. 2016; 24: 5803-5812. https://doi.org/10.1039/C6OB00192K
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