I8757
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:
Molecular Weight:
291.09
Beilstein:
4411317
MDL number:
UNSPSC Code:
12352209
PubChem Substance ID:
NACRES:
NA.26
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Product Name
4-Iodo-L-phenylalanine,
Assay
≥98.0% (TLC)
Quality Level
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
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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
S Samnick et al.
Nuclear medicine communications, 23(2), 121-130 (2002-03-14)
p-[123I]iodo-L-phenylalanine (IPA) is a recently described radiopharmaceutical which is highly accumulated in gliomas. The present investigation was designed to evaluate the feasibility of single photon emission tomography (SPET) with IPA to image brain tumours under routine clinical conditions. Using a
Koichiro Kodama et al.
Journal of biochemistry, 148(2), 179-187 (2010-05-25)
A variety of unique codons have been employed to expand the genetic code. The use of the opal (UGA) codon is promising, but insufficient information is available about the UGA suppression approach, which facilitates the incorporation of non-natural amino acids
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
Ina Israel et al.
Applied radiation and isotopes : including data, instrumentation and methods for use in agriculture, industry and medicine, 66(4), 513-522 (2007-11-21)
This work describes the synthesis and the tumor affinity testing of no-carrier-added (n.c.a.) p-[(124)I]iodo-L-phenyalanine ([(124)I]IPA) and n.c.a. p-[(131)I]iodo-l-phenyalanine ([(131)I]IPA) as radiopharmaceuticals for imaging brain tumors with PET and for radionuclid-based therapy, respectively. Parameters for labeling were optimized with regard to
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