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47306

Sigma-Aldrich

m-Fluoro-L-phenylalanine

≥99.0% (sum of enantiomers, HPLC)

Synonym(s):

3-Fluoro-L-phenylalanine

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About This Item

Empirical Formula (Hill Notation):
C9H10FNO2
CAS Number:
19883-77-3
Molecular Weight:
183.18
Beilstein:
2725762
MDL number:
MFCD00066450
UNSPSC Code:
12352200
PubChem Substance ID:
57650913
NACRES:
NA.22

Assay

≥99.0% (sum of enantiomers, HPLC)

optical activity

[α]20/D −25±2°, c = 1% in H2O

reaction suitability

reaction type: solution phase peptide synthesis

application(s)

peptide synthesis

SMILES string

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

InChI key

VWHRYODZTDMVSS-QMMMGPOBSA-N

Storage Class Code

13 - Non 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

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Certificates of Analysis (COA)

Lot/Batch Number
BCBM8683V
1442012
445756/1
264685/1

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T Ogawa et al.
European journal of nuclear medicine, 23(8), 889-895 (1996-08-01)
To elucidate the mechanism of large neutral amino acid (LNAA) transport in cerebral gliomas and to evaluate the clinical usefulness of positron emission tomography (PET) with fluorine-18 fluorophenylalanine (18F-Phe), we examined 18 patients with cerebral glioma using dynamic PET and
K Fukuda et al.
Current genetics, 20(6), 453-456 (1991-12-01)
o-Fluoro-DL-phenylalanine (OFP)-resistant mutants which overproduce beta-phenethyl-alcohol were isolated from a laboratory strain of Saccharomyces cerevisiae. Cells of one of the mutants accumulated tyrosine and phenylalanine 1.5-3 fold more than did wild-type cells. Its 3-deoxy-D-arabino-hepturosonate-7-phosphate (DAHP) synthase (EC 4.1.2.15), encoded by
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.
Jennifer C Jackson et al.
Journal of the American Chemical Society, 129(5), 1160-1166 (2007-02-01)
19F NMR is a powerful tool for monitoring protein conformational changes and interactions; however, the inability to site-specifically introduce fluorine labels into proteins of biological interest severely limits its applicability. Using methods for genetically directing incorporation of unnatural amino acids
M P Gamcsik et al.
FEBS letters, 196(1), 71-74 (1986-02-03)
Rabbits ingesting 4-fluorophenylalanine are known to incorporate small amounts of this fluorinated amino acid into their proteins. Carbonic anhydrase I isolated from the erythrocytes of animals so maintained exhibits a well-resolved fluorine NMR signal for each phenylalanine in the sequence.
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