4-Iodo-DL-Phenylalanine is an iodinated phenylalanine derivative in which the aromatic side chain bears an iodine substituent at the para (4-) position, and the molecule is supplied as a DL (racemic) mixture. It contains both an amino group and a carboxyl group on the alpha carbon, with the side chain functioning as an aryl iodide handle that can participate in halogen-based derivatization or labeling chemistry while maintaining the general phenylalanine scaffold for peptide incorporation studies. Researchers use this amino acid to introduce a defined aryl iodide functionality into peptide and small-molecule syntheses, supporting structure-activity studies, chemical labeling workflows, and analytical method development where a halogenated aromatic tag is required.
CAT No: CP15203
CAS No:14173-41-2
Synonyms/Alias:14173-41-2;2-amino-3-(4-iodophenyl)propanoicacid;4-IODO-DL-PHENYLALANINE;p-IODO-DL-PHENYLALANINE;4-Lodo-DL-phenylalanine;DL-P-IODOPHENYLALANINE;P-IODO-D-PHENYLALANINE;SBB063701;DL-4-iodophenylalanine;2-Amino-3-[4-iodophenyl]-propanoicacid;2-Amino-3-(4-iodophenyl)-propanoicacid;p-IODOPHENYLALANINE;ACMC-20ajvu;4-iodo-L-phenylalnine;PubChem14881;ACMC-209ga7;DL-Phe(3-I)-OH;AC1NP78G;SCHEMBL44618;294462_ALDRICH;MolPort-002-462-131;ANW-58878;CI-010;AKOS009158319;MCULE-3082140157
4-Iodo-DL-Phenylalanine is an iodinated phenylalanine derivative provided as a DL mixture, featuring an iodine substituent at the 4-position of the aromatic ring alongside the amino acid side chain. This halogenated, aromatic amino acid building block is commonly used in medicinal chemistry and chemical biology workflows where an aryl iodide serves as a chemically robust handle for further functionalization, including electrophilic aromatic substitution-derived diversification and metal-catalyzed coupling strategies. Its stereochemical DL configuration supports synthetic flexibility for downstream derivatization and comparative studies where enantiopure material is not required.
1. Medicinal Chemistry Building Block
4-Iodo-DL-Phenylalanine is used in structure-activity relationship (SAR) and analog development as an aryl iodide-containing amino acid building block for assembling substituted aromatic motifs. Medicinal chemistry groups and peptide/peptidomimetic developers rely on the iodine substituent as a functional handle for late-stage diversification, enabling rapid access to biaryl and aryl-substituted derivatives through standard coupling workflows. The presence of the amino acid functionality also allows incorporation into protected amino acid frameworks or further derivatization toward amino acid-based scaffolds used in lead optimization campaigns.
2. Peptidomimetic And Probe Synthesis
4-Iodo-DL-Phenylalanine supports the preparation of iodinated peptidomimetics and amino acid-containing chemical probes where the aromatic iodide provides a convenient site for downstream conjugation or derivatization. Chemical biology teams commonly select this type of halogenated amino acid building block when they want to introduce a defined aromatic substitution pattern into a larger probe scaffold while retaining the amino acid functionality for incorporation into peptide-like structures. The DL stereochemical form is frequently chosen for exploratory probe construction and comparative studies that prioritize substitution pattern control over stereochemical purity at the building-block stage.
3. Radiolabeling And Imaging Chemistry
4-Iodo-DL-Phenylalanine is used as a precursor in radiochemistry workflows where an aryl iodide motif is required for subsequent radiolabel introduction and downstream tracer synthesis. Radiochemistry and molecular imaging research groups value iodinated aromatic amino acid precursors because the iodine-bearing aromatic ring can be leveraged to generate radioiodinated derivatives for tracer development and labeling strategy screening. In these workflows, the amino acid framework helps maintain an amino-acid-like chemical identity while the iodination site supports the practical transition from precursor to labeled tracer candidates for analytical and method development.
4. Analytical Standard And Method Development
4-Iodo-DL-Phenylalanine is also applied as an analytical reference material and chemical standard in LC-MS and related characterization workflows that require an iodinated phenylalanine derivative. Analytical chemistry laboratories use this compound to support method qualification for iodinated amino acid derivatives, to verify retention and ionization behavior of halogenated aromatic species, and to calibrate or qualify identification workflows in complex mixtures. The defined iodination pattern at the 4-position makes it particularly useful when distinguishing closely related phenylalanine analogs in derivative-based analytical panels.
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