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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/REAXYS Number:
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

13 - Non Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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P Giusti et al.
European journal of pharmacology, 116(3), 287-292 (1985-10-22)
It had previously been shown that D-phenylalanine and hydrocinnamic acid, two in vitro inhibitors of carboxypeptidase A, possess an analgesic action when injected i.p. in mice. We have studied the in vivo effects of indole-3-acetic acid, another carboxypeptidase A inhibitor
Julianne L Kitevski-LeBlanc et al.
Journal of biomolecular NMR, 48(2), 113-121 (2010-08-25)
In protein NMR experiments which employ nonnative labeling, incomplete enrichment is often associated with inhomogeneous line broadening due to the presence of multiple labeled species. We investigate the merits of fractional enrichment strategies using a monofluorinated phenylalanine species, where resolution
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
[Transport of phenylalanine in human brain by L-[2-18F]-fluorophenylalanine and PET].
S Miura et al.
Nihon rinsho. Japanese journal of clinical medicine, 49(7), 1537-1540 (1991-07-01)
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.
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