3-Iodo-L-Phenylalanine is a halogenated, proteinogenic amino acid derivative featuring the L-phenylalanine backbone with an iodine substituent at the 3-position of the phenyl ring, yielding an aromatic side chain bearing a heavy halogen. The molecule contains a free amino group and a free carboxyl group along with a stereocenter consistent with the L-configuration indicated in the name, while the iodinated aromatic ring provides a distinct physicochemical handle for spectroscopic and chemical labeling contexts. It is used in peptide and amino acid chemistry as a substituted phenylalanine building block for structure-activity studies, as a precursor for further functionalization of the aryl iodide, and as an isotopically or chemically distinctive reagent for analytical method development and molecular probe preparation.
CAT No: CP15101
Synonyms/Alias:3-Iodo-L-Phenylalanine;20846-39-3;(S)-2-Amino-3-(3-iodophenyl)propanoic acid;L-Phenylalanine, 3-iodo-;(2S)-2-AMINO-3-(3-IODOPHENYL)PROPANOIC ACID;DTXSID00587780;(S)-2-Amino-3-(3-iodophenyl)propanoicacid;H-Phe(3-I)-OH;3-iodophenylalanine;L-3-Iodophe;MFCD01860664;m-iodo-L-phenylalanine;SCHEMBL159870;CHEMBL3808935;DTXCID90538544;STL573298;AKOS016843500;AS-58355;DB-328078;CS-0432660;F78754;Q27453519;33S;848-984-8;
3-Iodo-L-Phenylalanine is an iodinated, proteinogenic amino acid analog featuring an L-configured amino acid backbone and a para-position iodine substituent on the phenyl side chain. This heavy-atom functionalization makes it a practical building block for chemical biology workflows where halogen labeling, radiolabeling compatibility, or site-specific incorporation into peptides is required. In peptide and medicinal chemistry contexts, the aryl iodide also serves as a versatile handle for downstream derivatization while retaining the core amino acid recognition features used in synthetic and analytical setups.
1. Peptide Building Block Incorporation
3-Iodo-L-Phenylalanine is used as a site-specific amino acid building block for custom peptide synthesis where an iodinated aromatic residue is required for later functionalization or structural studies. Research groups developing halogenated peptide libraries, peptide ligands, or modified peptide probes rely on the L-configuration to maintain consistent stereochemical outcomes during peptide assembly. The aryl iodide on the side chain provides a convenient chemical handle for post-synthetic modification strategies, enabling access to iodinated analogs and further derivatized aromatic functionalities without changing the peptide backbone architecture.
2. Medicinal Chemistry Halogen Handle
3-Iodo-L-Phenylalanine is commonly selected in medicinal chemistry and SAR-focused synthesis programs that require an iodinated aromatic motif as a functional handle for derivatization. Medicinal chemistry teams use this residue to prepare halogenated analogs and to enable downstream coupling or substitution chemistry on the aromatic ring as part of iterative structure optimization. Because the compound is an amino acid derivative rather than a simple aryl iodide, it integrates more directly into peptide-like scaffolds and amino-acid-derived intermediates, supporting workflows where the aromatic iodide must be introduced with defined stereochemical context.
3. Radiolabeling and Imaging Chemistry
3-Iodo-L-Phenylalanine is used as a precursor for iodine-based radiolabeling strategies in research settings that require defined incorporation of an iodine atom into an amino acid framework. Chemical biology and tracer-development teams value the presence of the aryl iodide for preparing radiolabeled analogs used in binding studies, biodistribution experiments, and tracer optimization workflows. The amino acid format also supports downstream conjugation and scaffold construction, allowing the radiolabeled aromatic residue to be embedded into peptide-like constructs rather than relying solely on nonspecific iodination of aromatic fragments.
4. Analytical Standards for Iodinated Species
3-Iodo-L-Phenylalanine is applied as an analytical reference material for method development and quantitation involving iodinated amino acid species. Analytical chemistry laboratories use it to support LC-MS workflows, calibration strategies, and identification of iodinated metabolites or synthetic intermediates where an authentic iodinated amino acid is needed for retention-time and mass-based confirmation. Its defined structure helps reduce ambiguity when distinguishing iodinated aromatic species from non-iodinated analogs in complex sample matrices.
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