F5251
p-Fluoro-DL-phenylalanine
≥98.0% (TLC)
Synonym(s):
4-fluoro-phenylalanine
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About This Item
Linear Formula:
FC6H4CH2CH(NH2)COOH
CAS Number:
Molecular Weight:
183.18
NACRES:
NA.26
PubChem Substance ID:
eCl@ss:
32160406
UNSPSC Code:
12352209
EC Number:
200-113-7
MDL number:
Beilstein/REAXYS Number:
2938793
Product Name
p-Fluoro-DL-phenylalanine,
assay
≥98.0% (TLC)
Quality Level
form
powder
color
white to off-white
mp
253-255 °C (dec.) (lit.)
application(s)
peptide synthesis
SMILES string
NC(Cc1ccc(F)cc1)C(O)=O
InChI
1S/C9H10FNO2/c10-7-3-1-6(2-4-7)5-8(11)9(12)13/h1-4,8H,5,11H2,(H,12,13)
InChI key
XWHHYOYVRVGJJY-UHFFFAOYSA-N
Biochem/physiol Actions
Inhibits mitosis and reversibly arrests HeLa cells in G2.
p-Fluoro-DL-phenylalanine (pFPhe), a toxic antimetabolite, is a racemic mixture of a substituted (halogenated) benzoyl D and L phenylalanine useful as a selection marker for wine yeast transformation and with potential use in endomorphin, antiviral, and antimicrobial drug development. Phenylalanine analogue, rho-fluorophenylalanine (pFPhe) is also used to induce apoptosis.
signalword
Danger
hcodes
pcodes
Hazard Classifications
Acute Tox. 2 Oral
Storage Class
6.1A - Combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges
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Hae Sun Park et al.
Biochemical and biophysical research communications, 377(1), 280-285 (2008-10-11)
Phenylalanine analog, rho-fluorophenylalanine (pFPhe)-mediated cytotoxicity and several apoptotic events including mitochondrial cytochrome c release, activation of caspase-9, -3, and -8, Bid cleavage, degradation of PARP and PLCgamma-1, and DNA fragmentation were more significant in p56(lck)-deficient Jurkat T cells (JCaM1.6) than
Tomáš Štětina et al.
Insect biochemistry and molecular biology, 105, 60-68 (2019-01-21)
The biochemical and molecular mechanisms underlying insect cold acclimation prior to cold stress are relatively well explored, but the mechanisms linked to recovery and repair after cold stress have received much less attention. Here we focus on recovery from cold
Eduardo Cebollero et al.
Applied and environmental microbiology, 70(12), 7018-7023 (2004-12-03)
Genetic improvement of industrial yeast strains is restricted by the availability of selectable transformation markers. Antibiotic resistance markers have to be avoided for public health reasons, while auxotrophy markers are generally not useful for wine yeast strain transformation because most
H Kloosterman et al.
Microbiology (Reading, England), 149(Pt 11), 3321-3330 (2003-11-06)
Prephenate dehydratase (PDT), chorismate mutase (CM) and 3-deoxy-D-arabino-7-heptulosonate 7-phosphate (DAHP) synthase are key regulatory enzymes in aromatic amino acid biosynthesis in the actinomycete Amycolatopsis methanolica. Deregulated, feedback-control-resistant mutants were isolated by incubation of A. methanolica on glucose mineral agar containing
Jayapal Reddy Mallareddy et al.
Journal of medicinal chemistry, 54(5), 1462-1472 (2011-02-04)
This study reports on new proteolytically stable, pharmacologically active endomorphin analogues, incorporating Dmt(1), Achc(2), pFPhe(4), or βMePhe(4) unnatural amino acids. Consistent with earlier results, it was found that the analogues carrying Dmt(1) and Achc(2) residues displayed the highest μ-opioid receptor
Global Trade Item Number
| SKU | GTIN |
|---|---|
| F5251-1G | 04061826059326 |
| F5251-5G | 04061833618127 |
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