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F4505

Sigma-Aldrich

m-Fluoro-DL-tyrosine

≥98%, suitable for ligand binding assays

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Synonym(s):
3-fluoro-tyrosine
Linear Formula:
FC6H3-4-(OH)CH2CH(NH2)CO2H
CAS Number:
403-90-7
Molecular Weight:
199.18
EC Number:
206-964-0
MDL number:
MFCD00063075
UNSPSC Code:
12352209
PubChem Substance ID:
24894865
NACRES:
NA.26

Assay

≥98%

Quality Level

200

form

powder

technique(s)

ligand binding assay: suitable

color

white

mp

280 °C (dec.) (lit.)

storage temp.

2-8°C

SMILES string

NC(Cc1ccc(O)c(F)c1)C(O)=O

InChI

1S/C9H10FNO3/c10-6-3-5(1-2-8(6)12)4-7(11)9(13)14/h1-3,7,12H,4,11H2,(H,13,14)

InChI key

VIIAUOZUUGXERI-UHFFFAOYSA-N

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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.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H302 + H312 + H332

Hazard Classifications

Acute Tox. 4 Dermal - Acute Tox. 4 Inhalation - Acute Tox. 4 Oral

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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B Brooks et al.
Biochemistry, 37(27), 9738-9742 (1998-07-10)
Versions of the Y55F/Y88F modified form of Delta 5-3-ketosteroid isomerase in which the active-site tyrosine-14 is replaced by 2-fluorotyrosine, 3-fluorotyrosine, and 2,3-difluorotyrosine, amino acids having progressively greater acidity of their phenolic hydroxyls, have been expressed in an Escherichia coli host
Julianne L Kitevski-LeBlanc et al.
Journal of biomolecular NMR, 45(3), 255-264 (2009-08-06)
Fluorine NMR is a useful tool to probe protein folding, conformation and local topology owing to the sensitivity of the chemical shift to the local electrostatic environment. As an example we make use of (19)F NMR and 3-fluorotyrosine to evaluate
G Xiao et al.
Journal of molecular biology, 281(2), 323-339 (1998-08-12)
The structure of the tetradeca-(3-fluorotyrosyl) M1-1 GSH transferase (3-FTyr GSH transferase), a protein in which tyrosine residues are globally substituted by 3-fluorotyrosines has been determined at 2.2 A resolution. This variant was produced to study the effect on the enzymatic
S Jordan et al.
Brain research, 750(1-2), 264-276 (1997-03-07)
The tracer 6-[18F]fluoro-L-m-tyrosine (FMT) was studied with regard to its biochemistry and kinetics, as well as its utility in evaluating brain dopaminergic function in primates before and after 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine (MPTP) treatment using positron emission tomography (PET). Plasma analysis of FMT
Steven Y Reece et al.
Journal of the American Chemical Society, 128(42), 13654-13655 (2006-10-19)
The complex Re(bpy)(CO)3CN is an excited state oxidant of tyrosine upon deprotonation of the tyrosyl phenol. A series of Re(bpy-FnY)(CO)3CN complexes ([Re]-FnY: [Re]-Y, [Re]-3-FY, [Re]-3,5-F2Y, [Re]-2,3-F2Y, [Re]-2,3,5-F3Y, [Re]-2,3,6-F3Y, and [Re]-F4Y) have been prepared so as to vary the FnY*/FnY- reduction
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