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F5251

Sigma-Aldrich

p-Fluor-DL-phenylalanin

≥98.0% (TLC)

Synonym(e):

4-fluoro-phenylalanine

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About This Item

Lineare Formel:
FC6H4CH2CH(NH2)COOH
CAS-Nummer:
51-65-0
Molekulargewicht:
183.18
Beilstein:
2938793
EG-Nummer:
200-113-7
MDL-Nummer:
MFCD00002600
UNSPSC-Code:
12352209
eCl@ss:
32160406
PubChem Substanz-ID:
24894885
NACRES:
NA.26

product name

p-Fluor-DL-phenylalanin,

Assay

≥98.0% (TLC)

Form

powder

Farbe

white to off-white

mp (Schmelzpunkt)

253-255 °C (dec.) (lit.)

Anwendung(en)

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)

InChIKey

XWHHYOYVRVGJJY-UHFFFAOYSA-N

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Biochem./physiol. Wirkung

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.

Piktogramme

Skull and crossbones
GHS06

Signalwort

Danger

H-Sätze

H300

Gefahreneinstufungen

Acute Tox. 2 Oral

Lagerklassenschlüssel

6.1A - Combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials

WGK

WGK 3

Flammpunkt (°F)

Not applicable

Flammpunkt (°C)

Not applicable

Persönliche Schutzausrüstung

Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges

Analysenzertifikate (COA)

Suchen Sie nach Analysenzertifikate (COA), indem Sie die Lot-/Chargennummer des Produkts eingeben. Lot- und Chargennummern sind auf dem Produktetikett hinter den Wörtern ‘Lot’ oder ‘Batch’ (Lot oder Charge) zu finden.

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Sigma-Aldrich

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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
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
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
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