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I8757

Sigma-Aldrich

4-Iodo-L-phenylalanine

≥98.0% (TLC)

Synonym(s):

(S)-2-Amino-3-(4-iodophenyl)propanoic acid

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About This Item

Empirical Formula (Hill Notation):
C9H10INO2
CAS Number:
24250-85-9
Molecular Weight:
291.09
Beilstein:
4411317
MDL number:
MFCD00002602
UNSPSC Code:
12352209
PubChem Substance ID:
24896144
NACRES:
NA.26

product name

4-Iodo-L-phenylalanine,

Assay

≥98.0% (TLC)

form

powder

color

white to off-white

storage temp.

−20°C

SMILES string

N[C@@H](Cc1ccc(I)cc1)C(O)=O

InChI

1S/C9H10INO2/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

PZNQZSRPDOEBMS-QMMMGPOBSA-N

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Biochem/physiol Actions

4-Iodo-L-phenylalanine may be used in protein engineering as a model unnatural α amino acid to alter primary amino acid composition via the opal (UGA) codon.

Storage Class Code

11 - 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

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Veerle Kersemans et al.
European journal of nuclear medicine and molecular imaging, 33(8), 919-927 (2006-03-31)
In vitro in the R1M cell model and in vivo in the R1M tumour-bearing athymic model, both [(123)I]-2-iodo-L: -phenylalanine and [(123)I]-2-iodo-D: -phenylalanine have shown promising results as tumour diagnostic agents for SPECT. In order to compare these two amino acid
Koichiro Kodama et al.
Chembiochem : a European journal of chemical biology, 7(10), 1577-1581 (2006-09-14)
An Escherichia coli suppressor tRNA(Phe) (tRNA(Phe) (CUA)) was misacylated with 4-iodo-L-phenylalanine by using the A294G phenylalanyl-tRNA synthetase mutant (G294-PheRS) from E. coli at a high magnesium-ion concentration. The preacylated tRNA was added to an E. coli cell-free system and a
R Karthikraj et al.
Rapid communications in mass spectrometry : RCM, 26(11), 1385-1391 (2012-05-05)
In chiral differentiation by mass spectrometry, use of a single reference that differentiates various classes of compounds including drugs is ideal, but so far there are no such reports in the literature. We have successfully used iodo-substituted amino acids for
B Chevrier et al.
European journal of biochemistry, 237(2), 393-398 (1996-04-15)
The structure of the complex of Aeromonas proteolytica aminopeptidase, a two-zinc exopeptidase, with the inhibitor p-iodo-D-phenylalanine hydroxamate has been determined by X-ray crystallography. Refinement of the structure, which includes 220 water molecules, using data at 0.80-0.23-nm resolution resulted in a
Dirk Hellwig et al.
European journal of nuclear medicine and molecular imaging, 35(1), 24-31 (2007-09-12)
Radioactive amino-acids accumulate in gliomas even with an intact blood-brain-barrier. L-3-[(123)I]-iodo-alpha-methyl-tyrosine (IMT) is well established for SPECT imaging of gliomas. Recently, we introduced p-[(123)I]-iodo-L-phenylalanine (IPA) for the characterisation of brain lesions. This study compares both tracers in glioma patients. Eleven
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