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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)

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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D Hellwig et al.
Nuklearmedizin. Nuclear medicine, 47(5), 220-224 (2008-10-15)
Recently, p-[(123)I]iodo-L-phenylalanine (IPA) was clinically validated for brain tumour imaging. Preclinical studies demonstrated uptake of IPA into pancreatic adenocarcinoma suggesting its diagnostic application in patients with pancreatic tumours. The aim was to study the tumour uptake of IPA in patients
Samuel Samnick et al.
European journal of nuclear medicine and molecular imaging, 31(4), 532-541 (2004-01-15)
Pancreatic cancer is associated with the worst 5-year survival rate of any human cancer. This high mortality is due, in part, to difficulties in establishing early and accurate diagnosis. Because most tumours share the ability to accumulate amino acids more
D R Harding et al.
International journal of peptide and protein research, 26(2), 208-213 (1985-08-01)
The amino terminal fragment (1-15) of apolipoprotein C-1, H-Thr-Pro-Asp-Val-Ser-Ser-Ala-Leu-Asp-Lys-Leu-Lys-Glu-Phe14-Gly was prepared by the solid phase method. However, the phenylalanine residue at position 14 was replaced with p-iodophenylalanine in the chemical synthesis. The preparation of t-butyloxy-carbonyl-p-iodophenylalanine is described. After completion of
V Reiland et al.
Acta crystallographica. Section D, Biological crystallography, 60(Pt 10), 1738-1746 (2004-09-25)
The bacterial aminopeptidase isolated from the extracellular extract of Streptomyces griseus (SGAP) is a double-zinc exopeptidase with a high preference for large hydrophobic amino-terminus residues. It is a monomer of a relatively low molecular weight (30 kDa), is heat-stable, displays
Jianming Xie et al.
Nature biotechnology, 22(10), 1297-1301 (2004-09-21)
A recently developed method makes it possible to genetically encode unnatural amino acids with diverse physical, chemical or biological properties in Escherichia coli and yeast. We now show that this technology can be used to efficiently and site-specifically incorporate p-iodo-L-phenylalanine
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