EMAIL THIS PAGE TO A FRIEND

F4505 Sigma

m-Fluoro-DL-tyrosine

Purchase

Properties

Related Categories A - H, Amino Acids, Biochemicals and Reagents, Modified Amino Acids
mp   280 °C (dec.)(lit.)
storage temp.   2-8°C

Description

Biochem/physiol Actions

M-Fluorotyrosine (m-Fluoro-DL-tyrosine) may be substituted for tyrosine in the biosynthesis of proteins such as β-galactosidases (Escherichia coli), bacteriorhodopsin and intestinal microvillar enzymes, eg. aminopeptidase N, to study the effect of halogenated tryosines on the proteins properties.

Price and Availability

Suggested Laboratory Gloves


Laboratory GlovesThis substance has been tested against several types of hand protection for CE compliance. Click below to find the recommended gloves for handling this product.



Safety & Documentation

Safety Information

Symbol 
GHS07  GHS07
Signal word 
Warning
Hazard statements 
Precautionary statements 
Personal Protective Equipment 
WGK Germany 
3
RTECS 
YP2660000

Protocols & Articles

Peer-Reviewed Papers

References

Set your institution to view full text papers.

Perturbation of intestinal microvillar enzyme biosynthesis by amino acid analogs. Evidence that dimerization is required for the transport of aminopeptidase N out of the endoplasmic reticulum. Danielsen EM. J. Biol. Chem. 265, 14566-14571, (1990)

Loading...


The properties of β-galactosidases (Escherichia coli) with halogenated tyrosines. Ring M, Huber RE. Biochem. Cell Biol. 71, 127-132, (1993)

Loading...


Biosynthetic incorporation of m-fluorotyrosine into bacteriorhodopsin. Hazard ES 3rd, Govindjee R, Ebrey TG, Crouch RK. Photochem. Photobiol. 56, 929-934, (1992)

Loading...


Approaches for the measurement of solvent exposure in proteins by 19F NMR. Kitevski-LeBlanc JL, Evanics F, and Prosser RS J. Biomol. NMR 45(3), 255-64, (2009)

Loading...


Probing the coupling between proton and electron transfer in photosystem II core complexes containing a 3-fluorotyrosine. Rappaport F, Boussac A, Force DA, et al. J. Am. Chem. Soc. 131(12), 4425-33, (2009)

Loading...


A mutagenesis-free approach to assignment of (19)F NMR resonances in biosynthetically labeled proteins. Kitevski-LeBlanc JL, Al-Abdul-Wahid MS, and Prosser RS J. Am. Chem. Soc. 131(6), 2054-5, (2009)

Loading...


Positron emission tomography with 4-[18F]fluoro-L-m-tyrosine in MPTP-induced hemiparkinsonian monkeys. Hayase N, Tomiyoshi K, Watanabe K, et al. Ann. Nucl. Med. 9(3), 119-23, (1995)

Loading...


In vivo metabolism and partitioning of 6-[18F]fluoro-L-meta-tyrosine in whole blood: a unified compartment model. Asselin MC, Wahl LM, Cunningham VJ, et al. Phys. Med. Biol. 47(11), 1961-77, (2002)

Loading...


Mono-, di-, tri-, and tetra-substituted fluorotyrosines: new probes for enzymes that use tyrosyl radicals in catalysis. Seyedsayamdost MR, Reece SY, Nocera DG, et al. J. Am. Chem. Soc. 128(5), 1569-79, (2006)

Loading...


Site-specific incorporation of fluorotyrosines into the R2 subunit of E. coli ribonucleotide reductase by expressed protein ligation. Seyedsayamdost MR, Yee CS, and Stubbe J Nat. Protoc. 2(5), 1225-35, (2007)

Loading...


Mechanistic imperatives for the evolution of glutathione transferases. Armstrong RN Curr. Opin. Chem. Biol. 2(5), 618-23, (1998)

Loading...


Electron transfer reactions of fluorotyrosyl radicals. Reece SY, Seyedsayamdost MR, Stubbe J, et al. J. Am. Chem. Soc. 128(42), 13654-5, (2006)

Loading...


Effects of divalent metal ions on the activity and conformation of native and 3-fluorotyrosine-PvuII endonucleases. Dupureur CM and Hallman LM Eur. J. Biochem. 261(1), 261-8, (1999)

Loading...


Site-specific incorporation of fluorotyrosines into proteins in Escherichia coli by photochemical disguise. Wilkins BJ, Marionni S, Young DD, et al. Biochemistry 49(8), 1557-9, (2010)

Loading...


19F NMR studies of alpha-synuclein conformation and fibrillation. Li C, Lutz EA, Slade KM, et al. Biochemistry 48(36), 8578-84, (2009)

Loading...


Hydrogen bonding in human manganese superoxide dismutase containing 3-fluorotyrosine. Ayala I, Perry JJ, Szczepanski J, et al. Biophys. J. 89(6), 4171-9, (2005)

Loading...


Conformational changes in the crystal structure of rat glutathione transferase M1-1 with global substitution of 3-fluorotyrosine for tyrosine. Xiao G, Parsons JF, Tesh K, et al. J. Mol. Biol. 281(2), 323-39, (1998)

Loading...


6-[18F]fluoro-L-m-tyrosine: metabolism, positron emission tomography kinetics, and 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine lesions in primates. Jordan S, Eberling JL, Bankiewicz KS, et al. Brain Res. 750(1-2), 264-76, (1997)

Loading...


Structural and spectral response of Aequorea victoria green fluorescent proteins to chromophore fluorination. Pal PP, Bae JH, Azim MK, et al. Biochemistry 44(10), 3663-72, (2005)

Loading...


Crystallographic evidence for isomeric chromophores in 3-fluorotyrosyl-green fluorescent protein. Bae JH, Paramita Pal P, Moroder L, et al. ChemBioChem. 5(5), 720-2, (2004)

Loading...


Structural mobility in human manganese superoxide dismutase. Quint P, Ayala I, Busby SA, et al. Biochemistry 45(27), 8209-15, (2006)

Loading...


High-efficiency incorporation in vivo of tyrosine analogues with altered hydroxyl acidity in place of the catalytic tyrosine-14 of Delta 5-3-ketosteroid isomerase of Comamonas (Pseudomonas) testosteroni: effects of the modifications on isomerase kinetics. Brooks B, Phillips RS, and Benisek WF Biochemistry 37(27), 9738-42, (1998)

Loading...


Noncoded amino acid replacement probes of the aspartate aminotransferase mechanism. Park Y, Luo J, Schultz PG, Kirsch JF. Biochemistry 36, 10517-10525, (1997)

Loading...


Tubulin-tyrosine ligase catalyzes covalent binding of 3-fluoro-tyrosine to tubulin: kinetic and [19F]NMR studies. Monasterio O, Nova E, López-Brauet A, et al. FEBS Lett. 374(2), 165-8, (1995)

Loading...


3-Fluorotyrosine as a complementary probe of hemoglobin structure and dynamics: a (19)F-NMR study of Synechococcus sp. PCC 7002 GlbN. Pond MP, Wenke BB, Preimesberger MR, et al. Chem. Biodivers. 9(9), 1703-17, (2012)

Loading...


Aminoacrylate intermediates in the reaction of Citrobacter freundii tyrosine phenol-lyase. Phillips RS, Chen HY, and Faleev NG Biochemistry 45(31), 9575-83, (2006)

Loading...


Evaluating the potential of fluorinated tyrosines as spectroscopic probes of local protein environments: a UV resonance Raman study. Reid PJ, Loftus C, and Beeson CC Biochemistry 42(8), 2441-8, (2003)

Loading...


Comparison of the folding mechanism of highly homologous proteins in the lipid-binding protein family. Ropson IJ, Boyer JA, Schaeffer BA, et al. Proteins 75(4), 799-806, (2009)

Loading...


Aldrich MSDS 1, 977:D / Corp MSDS 1 (1), 1731:A / FT-IR 2 (2), 2751:D / FT-IR 1 (2), 256:B / FT-NMR 1 (2), 1189:A / IR-Spectra (2), 873:H / IR-Spectra (3), 998:C / NMR-Reference 2 (2), 258:C / RegBook 1 (2), 1847:C / Sigma FT-IR 1 (1), 160:D / Structure Index 1, 296:D:3

Related Products

Technical Service:

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Bulk Ordering & Pricing:

Need larger quantities for your development, manufacturing or research applications?