Fmoc-3-Iodo-D-Phenylalanine is a protected, non-natural amino acid derivative in which the amino acid backbone is functionalized with an Fmoc (fluorenylmethoxycarbonyl) group and the side chain is a para-substituted phenylalanine bearing a 3-iodo substituent on the aromatic ring. The molecule contains an Fmoc-protected amino functionality and a free carboxylic acid, and its stereochemistry is specified as D at the alpha carbon, with the iodo substituent providing a halogenated aromatic handle for further chemical modification or incorporation into labeled structures. In peptide chemistry and chemical biology research, it is used as a stepwise building block for preparing modified peptides or peptide analogues via protected-amino-acid coupling strategies, and the aryl iodide enables downstream derivatization for conjugation, structure-activity studies, or analytical labeling workflows.
CAT No: CP15107
Fmoc-3-Iodo-D-Phenylalanine is an Fmoc-protected D-phenylalanine derivative bearing an iodine substituent at the meta (3-) position of the aromatic ring. The molecule contains a chiral amino acid backbone with the stereochemistry fixed as the D-configuration, while the aromatic iodide provides a distinct electrophilic handle for cross-coupling and late-stage functionalization. The Fmoc group stabilizes the amino functionality during peptide assembly and can be removed under standard base conditions to enable sequential peptide coupling. The combination of an aromatic iodide and a protected carboxyl-compatible amino acid framework makes the compound a chiral intermediate suited to both peptide building block preparation and downstream medicinal chemistry-like derivatization.
1. Peptide Synthesis
Fmoc-3-Iodo-D-Phenylalanine is used in peptide synthesis workflows where an aromatic, halogenated amino acid side chain is required for controlled incorporation into linear peptides and peptide fragments. The Fmoc-protected amine supports solid-phase peptide coupling, while the meta-iodo substituent remains available for subsequent diversification after chain assembly. The D-stereocenter enables stereochemically defined incorporation for studies that distinguish D/ L effects on folding, stability, and protease resistance. The resulting iodinated peptide scaffold can be carried into further functional group transformations to generate analog libraries for peptide science and peptidomimetic construction.
2. Side-Chain Functionalization
Fmoc-3-Iodo-D-Phenylalanine serves as a chiral aromatic iodide intermediate for side-chain functionalization in synthetic organic chemistry and medicinal chemistry-oriented research. The aryl iodide at the 3-position can undergo palladium-catalyzed cross-coupling to install substituents such as aryl, heteroaryl, or alkenyl groups, enabling structure-activity relationship exploration around the phenyl ring. The Fmoc-protected amino acid architecture allows orthogonal handling, where the amino protection strategy can be maintained during early steps and removed when peptide coupling or conjugation is needed. Downstream derivatization can produce diversified D-phenylalanine analogs and peptidomimetic fragments for fragment-based molecular design and scaffold refinement.
3. Drug Discovery Scaffolds
Fmoc-3-Iodo-D-Phenylalanine is applied in drug discovery and SAR studies as an amino acid-based chiral scaffold that introduces an aryl halide for late-stage diversification. The D-configuration provides a stereochemically defined backbone for mapping stereochemical contributions to binding and metabolic stability concepts, while the iodinated aromatic ring supports rapid generation of substituted analogs through coupling chemistry. The Fmoc group functions as a protected amino handle that can be integrated into peptide-like inhibitors, constrained peptidomimetics, or hybrid small-molecule/peptide frameworks. The compound thereby supports iterative synthesis of structure-defined libraries that can be carried into biochemical target engagement studies without changing the core chiral amino acid motif.
4. Bioconjugation Handles
Fmoc-3-Iodo-D-Phenylalanine is suitable for bioconjugation chemistry where an iodinated aromatic motif can be converted into functional groups for attachment to biomolecular targets. The amino acid backbone and Fmoc protection enable preparation of defined peptide conjugates or linker-containing intermediates, with deprotection enabling controlled coupling to other building blocks. The aryl iodide can be transformed into conjugation-ready substituents through cross-coupling or further derivatization, supporting the construction of labeled peptides, affinity probes, or biomolecule-modified materials. The stereodefined D-phenylalanine unit can also help maintain structural integrity in conjugates used for chemical biology experiments and biomolecule modification workflows.
5. Process Chemistry Intermediate
Fmoc-3-Iodo-D-Phenylalanine functions as a chiral intermediate in process chemistry and specialty chemical production where protected amino acid derivatives are manufactured for downstream coupling and diversification steps. The Fmoc protecting group provides a stable, standardizable protection strategy for the amino functionality during handling, storage, and intermediate conversion, while the aromatic iodide offers a controllable reactive site for later transformation. The presence of a single, well-defined stereocenter supports reproducible incorporation into peptide building blocks and minimizes stereochemical ambiguity in scale-up routes. The compound can be employed as a manufacturing intermediate for generating iodinated amino acid derivatives, peptide analogs, and cross-coupling-ready building blocks used in fine chemical synthesis.
6. Analytical Research Standards
Fmoc-3-Iodo-D-Phenylalanine is utilized in analytical research as a stereochemically defined, iodinated amino acid reference material for method development and characterization of peptide and amino acid derivatives. The combination of Fmoc protection and the meta-iodo aromatic group provides distinctive mass and fragmentation features that can assist in LC-MS/MS identification of D-phenylalanine-containing species. The fixed D stereochemistry supports calibration and validation when stereochemical assignment or chiral purity assessment is required for peptide synthesis monitoring. The compound can also serve as a starting point for generating structurally related standards and internal references used to track derivatization, coupling efficiency, and downstream transformation of iodinated amino acid motifs.
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