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I8757

Sigma-Aldrich

4-Iodo-L-phenylalanine

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

Assay

≥98.0% (TLC)

Quality Level

200

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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Sigma-Aldrich

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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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