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F4505

Sigma-Aldrich

m-Fluoro-DL-tyrosine

≥98%, suitable for ligand binding assays

Synonym(s):

3-fluoro-tyrosine

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About This Item

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

product name

m-Fluoro-DL-tyrosine,

assay

≥98%

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

signalword

Warning

Hazard Classifications

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

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

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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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
Mohammad R Seyedsayamdost et al.
Journal of the American Chemical Society, 128(5), 1569-1579 (2006-02-02)
A set of N-acylated, carboxyamide fluorotyrosine (F(n)()Y) analogues [Ac-3-FY-NH(2), Ac-3,5-F(2)Y-NH(2), Ac-2,3-F(2)Y-NH(2), Ac-2,3,5-F(3)Y-NH(2), Ac-2,3,6-F(3)Y-NH(2) and Ac-2,3,5,6-F(4)Y-NH(2)] have been synthesized from their corresponding amino acids to interrogate the detailed reaction mechanism(s) accessible to F(n)()Y*s in small molecules and in proteins. These Ac-F(n)()Y-NH(2)
Prajna P Pal et al.
Biochemistry, 44(10), 3663-3672 (2005-03-09)
Global replacements of tyrosine by 2- and 3-fluorotyrosine in "enhanced green" and "enhanced yellow" mutants of Aequorea victoria green fluorescent proteins (avGFPs) provided protein variants with novel biophysical properties. While crystallographic and modeled structures of these proteins are indistinguishable from
M Ring et al.
Biochemistry and cell biology = Biochimie et biologie cellulaire, 71(3-4), 127-132 (1993-03-01)
An Escherichia coli tyrosine auxotroph (MR1) with an inducible lacZ was generated by mutagenesis. Of several tyrosine derivatives tested, only m-fluorotyrosine supported the growth of this mutant and allowed synthesis of active beta-galactosidase. The pH profiles of the beta-galactosidase that
Idelisa Ayala et al.
Biophysical journal, 89(6), 4171-4179 (2005-09-10)
Incorporation of 3-fluorotyrosine and site-specific mutagenesis has been utilized with Fourier transform infrared (FTIR) spectroscopy and x-ray crystallography to elucidate active-site structure and the role of an active-site residue Tyr34 in human manganese superoxide dismutase (MnSOD). Calculated harmonic frequencies at
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