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Sigma-Aldrich

o-Fluoro-DL-phenylalanine

≥98%

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About This Item

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

Storage Class Code

11 - Combustible Solids

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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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
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
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
H Ito et al.
Journal of nuclear medicine : official publication, Society of Nuclear Medicine, 36(7), 1232-1237 (1995-07-01)
Neutral amino acids (NAAs) are transported from the blood to the brain using the same carrier system in a competitive fashion. The purpose of this study is to establish a method for evaluating neutral amino acid transport at the blood-brain
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
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