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F4646

p-Fluoro-L-phenylalanine

Synonym(s):

4-Fluoro-L-phenylalanine

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About This Item

Empirical Formula (Hill Notation):
C9H10FNO2
CAS Number:
1132-68-9
Molecular Weight:
183.18
PubChem Substance ID:
24278435
UNSPSC Code:
12352200
Beilstein/REAXYS Number:
2416148
MDL number:
MFCD00063064
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SMILES string

N[C@@H](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)/t8-/m0/s1

InChI key

XWHHYOYVRVGJJY-QMMMGPOBSA-N

Gene Information

human ... TH(7054)
mouse ... TH(21823)
rat ... TH(25085)

General description

Substrate for tyrosine hydroxylase that has been used to study the regulation of that enzyme. Substitution of p-fluorophenylalanine for phenylalanine in the culture medium inhibits mitosis and reversibly arrests HeLa cells in G2.

pictograms

Skull and crossbones
GHS06

signalword

Danger

hcodes

H300

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, Gloves, type N95 (US)

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
SLBG6325V
041M1292V
011M1515V
031M1260V
120M1450

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Elisa Benetti et al.
Metabolites, 10(5) (2020-05-24)
Recent findings indicate a significant association between sedentary (SED)-time and type 2 diabetes mellitus(T2DM). The aim of this study was to investigate whether different levels of SED-time could impact on biochemical and physiological processes occurring in sedentary and physically inactive
P S Sunkara et al.
European journal of cell biology, 23(2), 312-316 (1981-02-01)
One of the objectives of this study was to develop a method for the reversible arrest of HeLa cells in G2 phase by using p-fluorophenylalanine (FPA), an analog of phenylalanine. Addition of 0.5 mM of FPA to synchronized HeLa cells
P J Hillas et al.
Biochemistry, 35(22), 6969-6975 (1996-06-04)
The iron-containing enzyme tyrosine hydroxylase catalyzes the hydroxylation of tyrosine to dihydroxyphenylalanine. A series of 4-X-substituted (X = H, F, Br, Cl, CH3, or CH3O) phenylalanines have been characterized as substrates to gain insight into the mechanism of hydroxylation. Multiple
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