Cbz-3-Iodo-D-Phenylalanine is a Cbz-protected, D-configured phenylalanine derivative bearing an iodine substituent at the 3-position of the aromatic side chain, placing it within the class of protected non-natural/halogenated amino acid analogues used for peptide-related chemistry. The molecule contains a free carboxyl group and an N-terminus protected as a benzyloxycarbonyl (Cbz) carbamate, while the aromatic ring bears a 3-iodo functionality that provides a halogenated handle for subsequent derivatization or incorporation into structured analog libraries. In synthesis, the Cbz protection supports chemoselective handling of the amino functionality during peptide coupling workflows, and the aryl iodide enables labeling, cross-coupling, or structure-activity studies of halogen-substituted aromatic residues in chemical biology and protein engineering contexts.
CAT No: CP15109
Cbz-3-Iodo-D-Phenylalanine is a Cbz-protected D-phenylalanine derivative bearing an iodine substituent at the 3-position of the aromatic ring, providing a chiral amino acid framework with a benzyl carbamate (Cbz) protecting group on the α-amino function. The molecule combines a stereodefined α-carbon (D-configuration) with an aryl iodide handle that can participate in electrophilic aromatic substitution, halogen-metal exchange, cross-coupling, and nucleophilic substitution under appropriate conditions. The carbamate carbonyl and aromatic iodide together influence reactivity selectivity during peptide coupling and subsequent functionalization, while the aromatic ring supports π-stacking and conformational bias in peptide and peptidomimetic contexts. As a halogenated protected amino acid intermediate, Cbz-3-Iodo-D-Phenylalanine is suited to building stereochemically defined peptide segments and to preparing downstream aryl-functionalized derivatives for synthetic and biochemical research.
1. Peptide Synthesis
Cbz-3-Iodo-D-Phenylalanine is applied in peptide building workflows where a protected amino acid with a stable Cbz carbamate enables controlled N-activation and coupling to form amide bonds at the α-position. The D-configuration at the stereogenic center supports incorporation of D-amino acid residues into peptides to modulate backbone conformation, protease resistance, and side-chain presentation. The aryl iodide substituent remains a latent functional handle that can be retained through coupling and then transformed later to install additional substituents or to generate aryl linkers. Downstream, the resulting iodinated peptide fragments can serve as intermediates for peptidomimetic libraries and for structure-activity relationship studies where aromatic substitution patterns are varied.
2. Cross-Coupling Functionalization
Cbz-3-Iodo-D-Phenylalanine is utilized as a chiral aryl iodide intermediate for palladium- and copper-mediated cross-coupling chemistry in synthetic organic chemistry and process-oriented fine chemical synthesis. The iodine substituent on the phenyl ring provides a direct electrophilic site for Suzuki, Sonogashira, and Buchwald-Hartwig-type transformations, allowing installation of heteroaryl groups, alkynyl motifs, or substituted anilines while maintaining the Cbz-protected amino acid scaffold. The Cbz group can be carried through coupling steps as a protecting-group strategy, with deprotection performed after aryl diversification when required for peptide coupling or conjugation. The stereodefined D-amino acid core supports generation of chiral, aryl-substituted derivatives used as synthetic intermediates for medicinal chemistry-style scaffolds and for downstream peptide analog construction.
3. Chemical Biology Labeling
Cbz-3-Iodo-D-Phenylalanine is suitable for chemical biology workflows that require incorporation of a functional aromatic handle into peptide-like structures for subsequent derivatization and probe construction. The protected amino acid form supports stepwise assembly into peptide fragments, while the aryl iodide enables post-assembly functionalization to introduce tags, affinity motifs, or reactive groups through cross-coupling or related aryl substitution strategies. The D-amino acid stereochemistry can be leveraged to tune stability and reduce enzymatic degradation of probe peptides used in biochemical assays and target-interaction mapping. Following iodide transformation, the resulting aryl-functionalized residues can be used to generate labeled biomolecule conjugates and to support mechanistic studies where side-chain electronics and sterics influence molecular recognition.
4. Peptidomimetics And SAR Studies
Cbz-3-Iodo-D-Phenylalanine is applied in peptidomimetic design and structure-activity relationship research where controlled aromatic substitution on a D-phenylalanine scaffold helps map the impact of aryl electronics and steric bulk. The Cbz-protected amino acid format supports incorporation into peptide mimics through standard peptide coupling chemistry, while the D-configuration provides a stereochemical handle for backbone engineering and conformational control. The aryl iodide can be transformed into a range of substituted phenyl or heteroaryl groups, enabling systematic variation of side-chain identity without altering the α-amino acid stereocenter. The resulting iodinated or aryl-diversified analogs function as research intermediates for SAR panels and for generating structure-defined libraries used to interrogate binding modes and physicochemical trends.
5. Pharmaceutical Intermediate Preparation
Cbz-3-Iodo-D-Phenylalanine is relevant to pharmaceutical intermediate preparation and specialty chemical production where chiral, protected amino acid derivatives serve as feedstocks for downstream active-ingredient-like fragments. The Cbz carbamate provides a robust N-protection strategy compatible with many synthetic steps, supporting manufacturing route designs that require selective functionalization at the aromatic ring before final deprotection and coupling. The aryl iodide functionality enables late-stage diversification, which can be used to access substituted aromatic motifs encountered in drug-like structures and in process chemistry intermediate sets. The stereodefined D-amino acid core supports consistent impurity profiles tied to stereochemical integrity across batch synthesis and subsequent transformations. Downstream, aryl-functionalized D-phenylalanine derivatives can be converted into peptide-linked or peptidomimetic intermediates for fine chemical manufacturing.
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