F5126
m-Fluoro-DL-phenylalanine
≥98%
Synonym(s):
3-Fluoro-DL-phenylalanine
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About This Item
Linear Formula:
FC6H4CH2CH(NH2)COOH
CAS Number:
Molecular Weight:
183.18
Beilstein:
2939807
EC Number:
MDL number:
UNSPSC Code:
12352209
PubChem Substance ID:
NACRES:
NA.26
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Product Name
m-Fluoro-DL-phenylalanine,
Assay
≥98%
Quality Level
form
powder
color
white to off-white
mp
240-250 °C
application(s)
cell analysis
peptide synthesis
SMILES string
NC(Cc1cccc(F)c1)C(O)=O
InChI
1S/C9H10FNO2/c10-7-3-1-2-6(4-7)5-8(11)9(12)13/h1-4,8H,5,11H2,(H,12,13)
InChI key
VWHRYODZTDMVSS-UHFFFAOYSA-N
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Biochem/physiol Actions
m-Fluoro-DL-phenylalanine, a toxic antimetabolite, is a racemic mixture of a substituted (halogenated) benzoyl D and L phenylalanine with potential use in antiviral and antimicrobial drug development.
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
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Nick J P Wierckx et al.
Applied and environmental microbiology, 71(12), 8221-8227 (2005-12-08)
Efficient bioconversion of glucose to phenol via the central metabolite tyrosine was achieved in the solvent-tolerant strain Pseudomonas putida S12. The tpl gene from Pantoea agglomerans, encoding tyrosine phenol lyase, was introduced into P. putida S12 to enable phenol production.
M P Gamcsik et al.
FEBS letters, 196(1), 71-74 (1986-02-03)
Rabbits ingesting 4-fluorophenylalanine are known to incorporate small amounts of this fluorinated amino acid into their proteins. Carbonic anhydrase I isolated from the erythrocytes of animals so maintained exhibits a well-resolved fluorine NMR signal for each phenylalanine in the sequence.
D H Young et al.
Experientia, 45(4), 325-327 (1989-04-15)
The tripeptide L-m-fluorophenylalanyl-L-alanyl-L-alanine was much more fungitoxic towards Pythium ultimum than the dipeptide L-m-fluorophenylalanyl-L-alanine or m-fluorophenylalanine. The fungitoxicity of the tripeptide was reduced by L-alanyl peptides and phenylalanine, but not by other amino acids. In contrast, the fungitoxicity of m-fluorophenylalanine
Jennifer C Jackson et al.
Journal of the American Chemical Society, 129(5), 1160-1166 (2007-02-01)
19F NMR is a powerful tool for monitoring protein conformational changes and interactions; however, the inability to site-specifically introduce fluorine labels into proteins of biological interest severely limits its applicability. Using methods for genetically directing incorporation of unnatural amino acids
H D Dettman et al.
Biophysical journal, 37(1), 243-251 (1982-01-01)
The nonlytic, filamentous coliphage M13 offers an excellent model system for the study of membrane-protein interactions. We prepare derivatives of the protein containing fluorine-labeled amino acids and use 19F nuclear magnetic resonance (NMR) to study the protein in both deoxycholate
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