2-Iodo-D-Phenylalanine is a non-natural halogenated amino acid derivative in which the phenylalanine backbone bears an iodine substituent at the 2-position relative to the amino acid carbon framework and is present in the D stereochemical form as indicated by the name. The molecule contains a primary amino group and a carboxyl group on the amino acid scaffold, while the side chain retains a substituted benzyl functionality with the ortho-iodo aryl feature that can participate in halogen-specific chemical transformations and provides a distinct mass and spectroscopic handle for analytical workflows. As a halogenated phenylalanine analogue, it is used in peptide and amino acid chemistry to introduce an aryl iodide functionality for structure-activity studies, chemical labeling or conjugation strategies, and isotopic or mass-based detection in biochemical and analytical method development.
CAT No: CP15002
2-Iodo-D-Phenylalanine is a D-configured, non-proteinogenic phenylalanine analog bearing an ortho-iodine substituent on the aromatic ring. This aryl iodide provides a chemically robust handle for downstream functionalization and is frequently selected in chemical biology and medicinal chemistry workflows where aromatic substitution pattern control matters. The stereodefined amino acid framework also supports its use as a defined building block for constructing peptidomimetics and labeled or derivatized aromatic motifs.
1. Medicinal Chemistry Building Block
2-Iodo-D-Phenylalanine is used by medicinal chemistry teams to access ortho-iodinated aromatic pharmacophores and to enable late-stage diversification of aromatic rings in lead optimization. The C2/ortho-iodine substituent offers a practical site for subsequent cross-coupling or electrophile-driven transformations during the synthesis of analog series, where maintaining the amino acid stereochemistry helps preserve defined spatial features in peptidomimetic scaffolds. This makes the compound a common choice for preparing defined intermediates for SAR studies, especially when the aromatic substitution pattern is a key structural variable.
2. Peptidomimetic And Analog Synthesis
2-Iodo-D-Phenylalanine is frequently employed in the synthesis of D-amino acid-containing peptides and peptidomimetics, where the D-configuration supports the incorporation of non-natural stereochemistry into bioactive or tool compounds. The ortho-iodo functionality provides an additional structural element that can be carried through assembly or used to introduce further substituents after scaffold construction, enabling iterative design of aromatic side-chain environments. Researchers developing constrained or stereochemically defined analogs for structure-activity relationship work often select this building block to ensure both stereochemical fidelity and a functional aromatic handle.
3. Chemical Biology Labeling And Probes
2-Iodo-D-Phenylalanine is used in chemical biology for constructing defined aromatic labeling motifs and affinity/derivatization reagents that require an ortho-iodinated phenylalanine core. The aryl iodide enables downstream attachment of reporter groups or coupling partners through established derivatization strategies, supporting the preparation of site-specifically modified probes and standards. In practice, teams working on small-molecule/biomolecule conjugation workflows value the combination of a stereodefined amino acid backbone and a stable aromatic leaving group for controlled probe synthesis.
4. Cross-Coupling Intermediate Development
2-Iodo-D-Phenylalanine serves as a high-value intermediate for preparing a variety of substituted aromatic derivatives via coupling-based synthetic routes. Pharmaceutical intermediate development groups and specialty chemical manufacturers rely on the ortho-iodine as a predictable functional handle to introduce new substituents while retaining the D-amino acid motif for subsequent downstream assembly. This approach is particularly relevant when the iodinated aromatic position must be preserved during early stages and later diversified to generate compound libraries with controlled substitution patterns.
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