Cbz-4-Iodo-L-Phenylalanine is a Cbz-protected, halogenated amino acid derivative featuring an L-phenylalanine backbone bearing a 4-iodo substituent on the aromatic side chain. The molecule contains a free carboxylic acid and an N-terminus protected as a benzyloxycarbonyl (Cbz) carbamate, with the aromatic ring bearing iodine at the para position to provide a heavier halogen handle for further chemical manipulation. As a protected amino acid suitable for stepwise peptide synthesis and for chemical biology labeling strategies, it can be used to introduce an aryl iodide functionality into peptide frameworks or to support subsequent coupling, conjugation, or derivatization workflows where the preserved aromatic iodide is retained.
CAT No: CP15208
Cbz-4-Iodo-L-Phenylalanine is an L-phenylalanine derivative bearing a benzyloxycarbonyl (Cbz) protecting group on the amino function and a para-iodo substituent on the aromatic ring. The molecule retains the stereogenic center of the amino acid backbone, providing a defined L-configuration for stereochemically controlled peptide coupling and downstream derivatization. The Cbz group and the carboxylic acid functionality (as present in the amino acid scaffold) support standard protected amino acid chemistry, while the aryl iodide enables carbon-carbon and carbon-heteroatom bond formation under halogen-reactivity conditions. The combination of a protected amine, a reactive aryl iodide, and an amino acid framework makes the compound suitable as a chiral aromatic building block for peptide science, radiolabeling-adjacent synthesis, and industrial fine chemical intermediate preparation.
1. Peptide Synthesis
Cbz-4-Iodo-L-Phenylalanine supports peptide building block preparation in solid-phase or solution-phase workflows where N-Cbz protection is compatible with common coupling strategies. The L-configuration at the α-carbon and the protected amine facilitate stereodefined amide bond formation, while the para-iodo aromatic side chain serves as a handle for later functionalization of the peptide residue. Cbz protection can be removed under established deprotection conditions to expose the free amine for subsequent coupling steps or for generating peptide fragments with defined termini. The aryl iodide can be carried through initial peptide assembly and then converted into diversified aromatic motifs, enabling iterative synthesis of iodinated or aryl-substituted peptide analogs. The amino acid scaffold also integrates cleanly into broader amino acid chemistry for constructing chiral, side-chain-modified peptide libraries.
2. Side-Chain Functionalization
Cbz-4-Iodo-L-Phenylalanine is well suited to side-chain functionalization strategies that exploit the para-iodo substituent as a cross-coupling precursor. The aryl iodide can participate in palladium-catalyzed transformations to introduce substituents such as aryl, heteroaryl, or alkenyl groups, allowing controlled modification of the phenylalanine side chain without disturbing the amino acid stereocenter. The Cbz-protected amine and carboxyl group support selective derivatization sequences where aromatic modification can be performed while maintaining peptide-coupling readiness for later conversion into amide-linked products. The resulting functionalized aromatic amino acid derivatives can be used to generate peptidomimetics with tailored hydrophobicity, electronic character, and binding-site interactions. This chemistry aligns with synthetic organic chemistry needs for chiral intermediate diversification and downstream scaffold expansion.
3. Chemical Biology Labeling
Cbz-4-Iodo-L-Phenylalanine can be applied in chemical biology workflows that require incorporation of an iodinated aromatic residue into peptide or protein-mimetic constructs. The protected amino acid form enables controlled incorporation during peptide synthesis, while the aryl iodide provides a reactive site for subsequent labeling or conjugation chemistry depending on the chosen transformation route. The L-configuration and Cbz protection help preserve stereochemical fidelity during assembly of labeled fragments, supporting consistent molecular recognition in biochemical assays. The compound's functional group set also supports the preparation of iodinated standards and molecular probes used for method development in biochemical research. Downstream derivatives derived from the iodide handle can serve as intermediates for generating conjugatable aromatic motifs and for mapping structure-function relationships in peptide-based systems.
4. SAR Studies
Cbz-4-Iodo-L-Phenylalanine is suitable for structure-activity relationship studies where systematic variation of an aromatic side chain is needed while keeping the amino acid backbone constant. The para-iodo substituent provides a defined chemical "switch" that can be transformed into multiple aryl or heteroaryl analogs, enabling parallel synthesis of closely related chiral variants. The Cbz-protected amino group supports consistent peptide coupling and allows the iodinated residue to be introduced at specific positions within peptide analogs for comparative evaluation. Stereochemical retention at the α-carbon helps ensure that observed changes in molecular behavior correlate with side-chain modification rather than backbone scrambling. The compound therefore functions as a chiral aromatic intermediate for generating SAR-focused libraries and for producing well-defined analogs for analytical characterization.
5. Pharmaceutical Manufacturing
Cbz-4-Iodo-L-Phenylalanine can be used as a process-relevant intermediate in the manufacturing of protected amino acid derivatives and peptide intermediates that contain a para-functionalized aromatic residue. The Cbz-protected amine supports robust handling as a stable N-protected amino acid, and the defined L-stereochemistry supports predictable coupling behavior in downstream amide formation steps. The aryl iodide enables manufacturing route design that may include late-stage aromatic diversification to reach specific intermediate specifications without changing the protected amino acid core. The compound's functional group profile supports integration into fine chemical synthesis sequences where orthogonal protection and selective transformations are required to manage multi-step production. The resulting iodide-derived intermediates can be further converted into aryl-substituted building blocks used in peptide or peptidomimetic manufacturing pipelines.
6. Analytical Research Standards
Cbz-4-Iodo-L-Phenylalanine serves as a useful analytical research standard and reference intermediate for method development involving iodinated amino acid derivatives and protected peptide building blocks. The presence of the Cbz group, the L-phenylalanine backbone, and the para-iodo aromatic substituent yields a distinct chemical signature that can support LC-MS or related analytical workflows when monitoring protected amino acid intermediates or coupling outcomes. The stereodefined amino acid structure helps ensure that analytical comparisons between L- and non-L variants remain unambiguous in stereospecific synthetic sequences. The aryl iodide moiety also enables preparation of structurally related reference compounds through controlled transformations, supporting comprehensive calibration sets for impurity profiling and identity testing. This role connects amino acid chemistry with applied analytical development for protected amino acid synthesis and downstream peptide science.
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