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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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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
H Ito et al.
Agricultural and biological chemistry, 54(3), 707-713 (1990-03-01)
Two kinds of 3-deoxy-D-arabino-hepturosonate-7-phosphate (DAHP) synthase genes were cloned from an L-Phe-producing mutant of Brevibacterium lactofermentum, AJ11957, which was resistant to m-fluoro-D,L-phenylalanine (mFP) and p-fluoro-D,L-phenylalanine (pFP) and which had DAHP synthase free from feedback inhibition. Both genes were cloned using
Julianne L Kitevski-LeBlanc et al.
Journal of biomolecular NMR, 48(2), 113-121 (2010-08-25)
In protein NMR experiments which employ nonnative labeling, incomplete enrichment is often associated with inhomogeneous line broadening due to the presence of multiple labeled species. We investigate the merits of fractional enrichment strategies using a monofluorinated phenylalanine species, where resolution
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 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
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