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F5126

Sigma-Aldrich

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:
456-88-2
Molecular Weight:
183.18
Beilstein:
2939807
EC Number:
220-104-1
MDL number:
MFCD00004273
UNSPSC Code:
12352209
PubChem Substance ID:
24894882
NACRES:
NA.26

product name

m-Fluoro-DL-phenylalanine,

Assay

≥98%

Quality Level

200

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

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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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.
Monica N Kinde et al.
Proceedings of the National Academy of Sciences of the United States of America, 113(48), 13762-13767 (2016-11-20)
Voltage-gated sodium channels (NaV) play an important role in general anesthesia. Electrophysiology measurements suggest that volatile anesthetics such as isoflurane inhibit NaV by stabilizing the inactivated state or altering the inactivation kinetics. Recent computational studies suggested the existence of multiple
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.
N Rastogi et al.
Antimicrobial agents and chemotherapy, 34(11), 2061-2064 (1990-11-01)
In the present work, we investigated whether resistance to isoniazid (INH) of organisms belonging to the Mycobacterium avium complex was caused by the bacterial cell envelope, with the cell wall and the outer layer acting as an exclusion barrier. We
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
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