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Merck
CN

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

Key Documents

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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

Regulatory Information

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Certificates of Analysis (COA)

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

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M S Chan et al.
Biochemical and biophysical research communications, 219(2), 537-542 (1996-02-15)
Corynebacterium glutamicum was mutated by nitrosoguanidine and five m-fluorophenylalanine (mFP)-resistant mutants were isolated. The mutants were resistant to phenylalanine-mediated feedback inhibition of the prephenate dehydratase activity. Cloning and characterization of the mFP-resistant gene revealed that mutant prephenate dehydratase, encoded by
N Rastogi et al.
Antimicrobial agents and chemotherapy, 34(11), 2061-2064 (1990-11-01)
In the present work, we investigated whether resistance to isoniazid (INH) of organisms belonging to the Mycobacterium avium complex was caused by the bacterial cell envelope, with the cell wall and the outer layer acting as an exclusion barrier. We
T T Otani et al.
Research communications in chemical pathology and pharmacology, 40(2), 321-324 (1983-05-01)
The fluoro-, chloro-, methoxy- and nitro-substituted benzoyl derivatives of m-fluoro-DL-phenylalanine, substituted singly at the ortho, meta or para position of the benzoyl phenyl ring, were prepared and tested for growth-inhibitory activity in a Lactobacillus casei system used as an antitumor
D H Young et al.
Experientia, 45(4), 325-327 (1989-04-15)
The tripeptide L-m-fluorophenylalanyl-L-alanyl-L-alanine was much more fungitoxic towards Pythium ultimum than the dipeptide L-m-fluorophenylalanyl-L-alanine or m-fluorophenylalanine. The fungitoxicity of the tripeptide was reduced by L-alanyl peptides and phenylalanine, but not by other amino acids. In contrast, the fungitoxicity of m-fluorophenylalanine
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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