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H-L-Phe(4-Eth)-OH*HCl
Chemical name: 4-Ethynyl-L-phenylalanine hydrochloride // Synonyms: H-Phe(4-Eth)-OH*HCl, (S)-1-carboxy-2-(4-ethynylphenyl)ethan-1-aminium, p-Ethynyl-L-phenylalanine hydrochloride, p-Ethynyl-phenylalanine hydrochloride, 4-Ethynyl-phenylalaninehydrochloride, para-Ethy nyl-Phe*HCl, para-Ethynyl-L-phenylalanine, pENF, P
- Product code:HAA9220
- CAS No.:188640-63-3
- Formula:C11H11NO2*HCl
- Storage temperature:-20°C
- Molecular weight:189.21*36.46 g/mol
from $250.00
description
This non canonical substituted phenylalanine contains a chemical handle, e.g. for post-translational biorthogonal conjugation reactions, e.g. by copper(I)-catalyzed azide-alkyne cycloadditions (CuAAC), an efficient Click Chemistry Reaction. CuAAC is orthogonal in the context of proteins and other cellular components, enabling applications in bacteria and mammalian cell lines.
references
Synthesis and Evaluation of Clickable Block Copolymers for Targeted Nanoparticle Drug Delivery; S. Zhang, K. H. Chan, R. K. Prud’homme, A. J. Link; Mol. Pharm. 2012; 9(8): 2228-2236. https://doi.org/10.1021/mp3000748.
Double Nitroxide Labeling by Copper-Catalyzed Azide-Alkyne Cycloadditions with Nanocanonical Amino Acids for Electron Paramagnetic Resonance Spectroscopy; P. Widder, F. Berner, D. Summerer, M. Drescher; ACS Chem. Biol. 2019; 14(5): 839-844. https://doi.org/10.1021/acschembio.8b01111.
Highly Constrained Bicyclic Scaffolds for the Discovery of Protease-Stable Peptides via mRNA Display; D. E. Hacker, J. Hoinka, E. S. Iqbal, T. M. Przytycka, M. C. T. Hartman; ACS Chem. Biol. 2017; 12(3): 795-804. https://doi.org/10.1021/acschembio.6b01006.
New Strategy for the Preparation of Clickable Peptides and Labeling with 1-(Azidomethyl)-4-[18F]-fluorobenzene for PET; D. Thonon, C. Kech, J. Paris, C. Lemaire, A. Luxen; Bioconjugate Chem. 2009; 20(4): 817-823. https://doi.org/10.1021/bc800544p.
Enzymatic N-terminal Addition of Noncanonical Amino Acids to Peptides and Proteins; R. E. Connor, K. Piatkov, A. Varshavsky, D. A. Tirrell; ChemBioChem 2008; 9(3): 366-369. https://doi.org/10.1002/cbic.200700605.
An Efficient Method for the Construction of Functionalized DNA Bearing Amino Acid Groups through Cross-Coupling Reactions of Nucleoside Triphosphates Followed by Primer Extension or PCR; P. Capek, H. Cahova, R. Pohl, M. Hocek, C. Gloeckner, A. Marx; Chem. Eur. J. 2007; 13(21): 6196-6203. https://doi.org/10.1002/chem.200700220.
Selective Dye-Labeling of Newly Synthesized Proteins in Bacterial Cells; K. E. Beaty, F. Xie, Q. Wang, D. A. Tirrell; J. Am. Chem. Soc. 2005; 127(41): 14150-14151. https://doi.org/10.1021/ja054643w.
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