Cbz-2-Iodo-D-Phenylalanine is a Cbz-protected, non-natural amino acid derivative featuring a D-configuration at the α-carbon and a phenylalanine-derived side chain bearing an ortho-iodine substituent on the aromatic ring. The molecule contains an N-Cbz carbamate protecting group on the amino functionality and a free carboxylic acid, with the iodinated aryl side chain providing a halogenated handle for chemoselective transformations and structure-activity or labeling studies. In peptide chemistry, the protected amino acid form supports stepwise coupling during peptide assembly in protected-amino-acid workflows, while the aryl iodide enables downstream derivatization routes used in synthesis of more complex aromatic amino acid analogues and conjugation targets.
CAT No: CP15009
Cbz-2-Iodo-D-Phenylalanine is a D-configuration phenylalanine derivative bearing an N-Cbz (benzyloxycarbonyl) protecting group and a stereogenic center at the alpha carbon substituted with iodine at the 2-position and a benzyl side chain at the 3-position. The molecule combines an aromatic ring system with a reactive carbon-iodine bond, enabling selective functional transformations while maintaining the amino acid framework for peptide chemistry. The Cbz carbamate provides stable protection under many coupling conditions and can be removed by hydrogenolysis or related deprotection strategies to regenerate the free amine for subsequent bond formation. The presence of the benzylic aromatic substituent and the iodine substituent influences reactivity and downstream derivatization, making the compound a chiral intermediate suited to stereodefined amino acid modification and C-X functional group chemistry.
1. Protected Amino Acid Coupling
Cbz-2-Iodo-D-Phenylalanine is used in protected amino acid synthesis and peptide coupling workflows where a stable N-protecting group is required for controlled amide-bond formation. The Cbz-protected amine and the carboxylate functionality characteristic of phenylalanine derivatives support standard peptide coupling logic after appropriate activation of the acid component, while the D-stereochemistry provides stereodefined incorporation into growing peptide chains. The carbon-iodine substituent can remain intact during coupling to preserve a handle for later side-chain or backbone functionalization after N-deprotection. Downstream, the resulting iodinated peptide intermediate can be converted into analogs bearing substituted aryl or heteroaryl motifs, enabling structure-activity relationship studies and chiral peptide library construction.
2. Chiral Iodinated Building Block
Cbz-2-Iodo-D-Phenylalanine is applied as a chiral iodo-amino acid intermediate for stereoselective synthetic organic chemistry and fragment elaboration. The C-I bond at the 2-position provides a direct electrophilic functional handle for substitution, cross-coupling, or nucleophile-mediated transformations that can proceed without disturbing the protected carbamate. The N-Cbz group helps maintain chemoselectivity by reducing undesired side reactions from the nitrogen during halogen-based derivatization steps. The D-configuration at the alpha carbon supports the preparation of diastereomer- and enantiomer-controlled derivatives used in medicinal chemistry-oriented scaffold diversification and stereochemically defined intermediate manufacturing.
3. Peptidomimetic And SAR Studies
Cbz-2-Iodo-D-Phenylalanine is suitable for peptidomimetic construction and structure-activity relationship studies where iodine-bearing amino acid analogs help probe binding-site tolerance to steric and electronic changes. The phenylalanine core and N-Cbz protection allow incorporation into peptide-like backbones, while the iodinated alpha position can serve as a precursor for conversion into substituted functionalities that modulate polarity, polarizability, and conformational preferences. The ability to retain the amino acid stereocenter during sequential protection, coupling, and late-stage functional group interconversions supports systematic SAR workflows in which analogs differ at a single stereodefined position. The iodinated intermediate can also be routed toward radio- or imaging-compatible analogs in research settings where halogen chemistry is leveraged for labeling strategies.
4. Chemical Biology Labeling
Cbz-2-Iodo-D-Phenylalanine is used in chemical biology research to introduce halogenated amino acid motifs into peptides or protein fragments for downstream conjugation or affinity probe development. The protected amine enables incorporation into biomolecule scaffolds through peptide coupling, while the carbon-iodine functionality can be transformed into reactive groups or substituted for click-compatible handles depending on the chosen derivatization route. The retained stereochemistry at the alpha carbon supports consistent molecular recognition when analogs are compared across a series. The resulting iodinated or derivatized amino acid-containing constructs can function as intermediates for biomolecule labeling, pull-down probes, or mechanistic studies of amino acid position effects on binding and processing.
5. Process Chemistry Intermediate
Cbz-2-Iodo-D-Phenylalanine is suitable for process chemistry intermediate preparation where controlled protection and robust functional group compatibility are required for scalable fine chemical synthesis. The Cbz carbamate offers a practical protection strategy for the amino functionality during multi-step manufacturing, while the iodine substituent provides a chemically reactive site that can be carried through protected stages and converted in later steps. The aromatic-rich phenylalanine framework can support predictable purification behavior relative to less protected or more polar intermediates, aiding route design for chiral amino acid derivative production. The compound can therefore serve as a stereodefined intermediate for industrial synthesis of iodinated amino acid derivatives, peptide building blocks, and downstream substituted analogs used in specialty chemical production and applied research manufacturing.
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