Cbz-2-Iodo-L-Phenylalanine is a Cbz-protected, L-phenylalanine-derived amino acid bearing an iodine substituent at the 2-position of the side chain aromatic ring. The molecule contains a carbobenzyloxy (Cbz) protecting group on the amino functionality, while the carboxyl group remains available as a free acid for coupling chemistry, and the aromatic ring features the iodo substituent as a halogenated functional handle. In peptide synthesis and structure-activity or chemical biology studies, this protected amino acid is used to introduce a halogenated phenylalanine residue into peptide frameworks and to support downstream labeling, conjugation, or analytical differentiation based on the iodine-bearing aromatic side chain.
CAT No: CP15008
Cbz-2-Iodo-L-Phenylalanine is a Cbz-protected L-phenylalanine derivative bearing an iodine substituent at the 2-position of the amino acid side chain (α-position relative to the carboxylate-bearing carbon is retained as L-configuration). The molecule contains a benzyloxycarbonyl (Cbz) carbamate on the amino group, a carboxylic acid functionality, and a stereodefined chiral center that supports predictable peptide-coupling behavior after activation. The aryl side chain and the ortho-iodinated stereochemical environment provide a distinct reactivity profile, combining peptide-compatible functional groups with a halogen handle suitable for cross-coupling and selective transformations. As a chiral amino acid intermediate, Cbz-2-Iodo-L-Phenylalanine can be used to prepare protected amino acid building blocks and downstream iodinated analogs for structure-driven synthesis.
1. Peptide Synthesis
Cbz-2-Iodo-L-Phenylalanine is used in peptide building block preparation where the Cbz-protected amine and carboxylic acid enable standard peptide coupling after appropriate activation. The L-stereochemistry at the amino acid backbone supports stereochemically consistent incorporation into peptide sequences, while the iodine substituent can be retained for post-coupling diversification or converted into other side-chain functionalities. Carbamate protection allows controlled deprotection conditions that can be orthogonal to other protecting groups during multistep solid-phase or solution-phase assembly. Downstream iodinated peptide analogs and peptidomimetic fragments can be generated for library construction and sequence-specific biochemical studies.
2. Chiral Cross-Coupling Intermediates
Cbz-2-Iodo-L-Phenylalanine is applied as a chiral aryl-iodide intermediate for stereodefined synthetic organic chemistry, leveraging the C-I bond for palladium-catalyzed coupling chemistry. The protected amino acid framework preserves the amino and carboxyl functionalities during halogen-functionalization steps, allowing conversion of the iodine handle into aryl, heteroaryl, or alkyl substituents while maintaining the L-configuration. Cbz protection can be maintained through coupling and later removed to expose the amine for subsequent derivatization or peptide coupling. The resulting substituted phenylalanine derivatives serve as downstream intermediates for SAR-focused scaffold diversification and functional group tuning.
3. Side-Chain Functionalization
Cbz-2-Iodo-L-Phenylalanine supports side-chain functionalization strategies in chemical biology and medicinal chemistry workflows that require controlled introduction of iodine-derived substituents. The iodine at the 2-position acts as a selective functional handle for transformation into groups such as boronic acid equivalents, pseudohalides, or substituted aryl/heteroaryl moieties, enabling systematic exploration of steric and electronic effects. The amino acid's protected carbamate and carboxylic acid allow sequential chemistry without uncontrolled polymerization or side reactions from free amine. Functionalized amino acid analogs prepared from this intermediate can feed into peptidomimetic construction, receptor-binding probes, and chemically defined biomolecular conjugation reagents.
4. Chemical Biology Probes
Cbz-2-Iodo-L-Phenylalanine is suitable for generating chemically defined probes and labeled analogs used in chemical biology research, where a stable amino acid scaffold is required for molecular recognition. The Cbz-protected amine and carboxylic acid support incorporation into peptide-like structures, while the iodine substituent can be used for subsequent derivatization to introduce imaging or affinity tags through cross-coupling-derived handles. Stereochemical fidelity of the L-amino acid backbone helps maintain conformational preferences relevant to peptide mimicry and binding studies. Downstream iodinated or substituted derivatives can be used as intermediates for probe synthesis and for constructing structure-activity relationship series.
5. Pharmaceutical Intermediate Preparation
Cbz-2-Iodo-L-Phenylalanine is employed as a process-relevant chiral intermediate in fine chemical synthesis where protected amino acid chemistry and halogen-functionalization are combined in a single stereodefined feedstock. The Cbz carbamate provides a robust amine protection strategy compatible with many coupling and functional group interconversion steps, while the carboxylic acid allows controlled conversion into activated derivatives for downstream assembly. The iodine substituent can be carried through manufacturing steps as a latent reactive group, then transformed into tailored substituents to meet specific intermediate specifications. The compound's structure aligns with the preparation of iodinated amino acid derivatives and peptide-building blocks used in industrial-scale synthesis of complex, stereochemically defined molecules.
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