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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%

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 G Hinds et al.
The Biochemical journal, 287 ( Pt 2), 627-632 (1992-10-15)
A fluorine-containing analogue of the cyclic AMP (cAMP) receptor protein (CRP) from Escherichia coli was prepared by biosynthetic incorporation of 3-fluorophenylalanine (3-F-Phe). 19F n.m.r. studies on this protein have provided direct evidence for cAMP-induced conformational changes not only within the
W D Kingsbury et al.
Journal of medicinal chemistry, 26(12), 1725-1729 (1983-12-01)
A series of di- and tripeptides containing D- and L-m-fluorophenylalanine was prepared and tested in vitro for the ability to inhibit the growth of the yeast Candida albicans. The results demonstrate that peptides containing L-m-fluorophenylalanine inhibited the growth of C.
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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