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47300

Sigma-Aldrich

o-Fluoro-DL-phenylalanine

≥98%

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Linear Formula:
FC6H4CH2CH(NH2)COOH
CAS Number:
2629-55-2
Molecular Weight:
183.18
Beilstein:
3201186
EC Number:
220-105-7
MDL number:
MFCD00004271
UNSPSC Code:
12352200
PubChem Substance ID:
57650911
NACRES:
NA.22

Assay

≥95% (NT)
≥98% (HPLC)
≥98%

form

powder

reaction suitability

reaction type: solution phase peptide synthesis

color

white to faint brown

mp

243-246 °C (lit.)

application(s)

cell analysis
peptide synthesis

SMILES string

NC(Cc1ccccc1F)C(O)=O

InChI

1S/C9H10FNO2/c10-7-4-2-1-3-6(7)5-8(11)9(12)13/h1-4,8H,5,11H2,(H,12,13)

InChI key

NYCRCTMDYITATC-UHFFFAOYSA-N

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Application

Reactant involved in:
  • Studying mechanism of P 450-mediated oxidation and rearrangement
  • Conversion of racemic α-arylalanines to (R)-β-arylalanines
  • Ribosomal translation of unnatural peptides
  • Synthesis of diisopropylpyridine acetamides for use as Kv1.5 potassium channel antagonists
  • Enantioselective hydrolysis of esters for resolution of nonprotein amino acids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

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Johnny Castillo Meleán et al.
Organic & biomolecular chemistry, 9(3), 765-769 (2010-11-23)
2-[(18)F]Fluoro-L-phenylalanine and 2-[(18)F]fluoro-L-tyrosine have been developed as promising radiopharmaceuticals for molecular imaging using positron emission tomography (PET). However, the lack of a convenient radiosynthetic pathway has limited their practical use. In this work a new three-step nucleophilic synthesis of these
K Kubota et al.
Journal of nuclear medicine : official publication, Society of Nuclear Medicine, 37(2), 320-325 (1996-02-01)
L-[methyl-11C]methionine (11C-Met) is a useful tracer for tumor imaging with PET. The drawbacks include a short half-life and high physiological accumulation in abdominal organs. To overcome these shortfalls, the feasible use of [18F]fluorophenylalanine (18F-Phe), which shares the same amino acid
Kensuke Okuda et al.
Biochemistry, 44(17), 6675-6684 (2005-04-27)
The ribosome-catalyzed peptidyl transferase reaction displays a complex pH profile resulting from two functional groups whose deprotonation is important for the reaction, one within the A-site substrate and a second unidentified group thought to reside in the rRNA peptidyl transferase
T T Otani et al.
Journal of pharmaceutical sciences, 71(2), 214-216 (1982-02-01)
Twelve derivatives of 0-fluoro-dl-phenylalanine containing fluorine, chlorine, methoxy, and nitro radicals in various positions of the aromatic ring of the benzoyl group were prepared and tested in a Lactobacillus casei system. It was found that most substitutions in the benzoyl
J Hatazawa et al.
Annals of nuclear medicine, 8(3), 213-217 (1994-08-01)
We studied the brain uptake of amino acid in a patient with acute cerebral infarction with L-[2-(F-18)]fluorophenylalanine and positron emission tomography. The increased accumulation of the ligand was specifically found in the peri-infarct area where oxygen metabolism was still maintained
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