Boc-3-Iodo-D-Phenylalanine is a protected, non-natural amino acid derivative featuring a benzyl side chain bearing an iodine substituent at the 3-position and a D stereochemical configuration at the α-carbon. The molecule contains both an amino function masked as a Boc (tert-butoxycarbonyl) carbamate and a free carboxylic acid, with the aryl iodide providing a halogenated handle for further chemical transformations while the aromatic ring contributes hydrophobic and π-interaction character. In peptide and amino acid chemistry workflows, this Boc-protected iodinated phenylalanine analogue is used as a building block for assembling iodinated peptide structures or for preparing more complex amino acid derivatives used in structure-activity studies, chemical labeling, and analytical method development.
CAT No: CP15105
Boc-3-Iodo-D-Phenylalanine is a D-configuration, Boc-protected phenylalanine derivative bearing an iodine substituent at the 3-position of the aromatic ring. This aryl-iodide functionality makes it a practical halogenated amino acid building block for downstream diversification, while the Boc protection supports its use as a protected amino acid intermediate in peptide and peptidomimetic synthesis workflows. Researchers select this scaffold when they need an aromatic iodide handle for chemoselective coupling strategies and controlled incorporation of a stereodefined amino acid residue.
1. Peptidomimetic Building Block
Boc-3-Iodo-D-Phenylalanine is used as a protected amino acid building block for assembling D-amino acid-containing peptidomimetics and non-natural peptide analogs where the aromatic iodide is retained for later functional diversification. Medicinal chemistry groups and custom synthesis providers often leverage the Boc-protected amine to integrate the residue into larger coupling sequences, then use the aryl-iodide as a strategic handle for subsequent carbon-carbon bond formation or aromatic substitution steps. The D-stereochemistry supports the construction of stereochemically defined analog libraries used in structure-activity relationship studies and protease/peptidase resistance evaluation workflows.
2. Late-Stage Aromatic Diversification
Boc-3-Iodo-D-Phenylalanine supports late-stage diversification of peptide fragments or small-molecule scaffolds through the presence of a reactive aryl iodide. In chemical biology and medicinal chemistry development, the iodinated aromatic ring enables coupling-based elaboration of the residue after initial assembly of the protected amino acid or peptide segment, helping teams rapidly explore substitution patterns without redesigning the entire synthetic route. The combination of a Boc-protected backbone and a stable aryl-iodide handle is particularly useful when the downstream workflow requires preserving the amino acid functionality while modifying the aromatic substitution to tune physicochemical properties or binding interactions.
3. Pharmaceutical Intermediate Development
Boc-3-Iodo-D-Phenylalanine is commonly used as a pharmaceutical intermediate in the preparation of iodinated aromatic amino acid derivatives and related chiral intermediates for medicinal chemistry programs. Process and development chemists value the stereodefined D-configuration and the Boc-protected amine as a controlled starting point for generating analog series that require an iodinated aryl motif for further synthetic elaboration. The product fits industrial intermediate development workflows where halogenated aromatic intermediates are used to access diverse substitution patterns while maintaining a consistent amino acid core for scale-up and parallel synthesis.
4. Analytical Reference Material Support
Boc-3-Iodo-D-Phenylalanine is also used as a reference building block for analytical method development and characterization of iodinated amino acid derivatives in LC-MS and related workflows. Laboratories developing assays for peptide fragments, iodinated intermediates, or coupling products often require authentic standards that contain both the protected amino acid backbone and the aryl iodide motif to confirm identity and monitor conversion during synthesis. The stereodefined D-amino acid scaffold further supports unambiguous interpretation when separating or tracking stereochemically defined intermediates across development stages.
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