3-Iodo-D-Phenylalanine is a halogenated, non-proteinogenic phenylalanine derivative featuring a benzyl side chain substituted with an iodine atom at the 3-position and bearing a free amino group and a free carboxyl group on the α-carbon framework. The molecule is specified as the D stereoisomer and presents an aromatic iodination handle alongside the primary amine and carboxylic acid functionalities, which can participate in standard amino-acid coupling chemistry while the iodine substituent supports chemical labeling or further derivatization. It is used as a substrate-like building block in peptide and amino-acid derivative synthesis and as an aromatic functionalized amino acid for chemical biology and analytical method development where a defined iodinated aromatic moiety is required.
CAT No: CP15102
3-Iodo-D-Phenylalanine is a halogenated, stereochemically defined amino acid building block featuring a D-configuration and an iodine substituent at the meta position of the phenyl side chain. Its aryl iodide functionality makes it a practical handle for downstream carbon-carbon and carbon-heteroatom bond formation, while the D-configuration supports incorporation into stereodefined peptide analogs and peptidomimetic structures used in chemical biology and medicinal chemistry programs. Because the aryl iodide is directly embedded in the amino acid side chain, it is commonly leveraged to introduce aryl-linked motifs during target-directed synthesis rather than relying on late-stage functionalization of a separate aromatic intermediate.
1. Peptidomimetic Building Block
3-Iodo-D-Phenylalanine is used by medicinal chemistry and chemical biology groups to prepare stereodefined peptide analogs and peptidomimetics where the meta-iodophenyl side chain serves as a site for selective aryl diversification. Researchers often incorporate this amino acid into custom peptide synthesis workflows to generate libraries of analogs with distinct aryl substituents, enabling structure-activity relationship studies that depend on controlled aromatic substitution patterns. The D-configuration supports the generation of non-proteinogenic, stereochemically defined sequences for mechanistic studies and lead optimization of peptide-like scaffolds.
2. Medicinal Chemistry Diversification
3-Iodo-D-Phenylalanine supports medicinal chemistry programs that require rapid installation of aryl-linked functional groups onto a phenylalanine-derived scaffold. The iodine substituent provides a chemically robust functional handle for subsequent coupling-based derivatization, allowing chemists to access aryl-substituted analogs without changing the amino acid backbone stereochemistry. This approach is particularly valuable when the aromatic substitution pattern must be preserved across a series of compounds, such as in SAR studies for small-molecule conjugates, kinase/ligand binding probes, or other receptor-targeted chemical biology tools where aryl electronics and substitution geometry are critical.
3. Radiolabeling and Imaging Probes
3-Iodo-D-Phenylalanine is used in research settings where iodinated aromatic amino acid motifs are required as precursors for iodine-based labeling strategies and probe construction. The presence of an aryl iodide enables workflows that generate iodinated derivatives for tracer development, including studies that track distribution or binding behavior of amino-acid-like motifs in biochemical assays and imaging-related experiments. Teams performing tracer chemistry and probe synthesis often select this building block to maintain the stereodefined D-phenylalanine framework while introducing iodine functionality needed for downstream radiochemistry or iodination-based probe generation.
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