Cbz-4-Iodo-D-Phenylalanine is a Cbz-protected, non-natural amino acid derivative in which the amino acid backbone is substituted with a 4-iodo functional group on the phenyl side chain, and the stereochemical form is specified as D. The molecule contains a free carboxyl group and a benzyloxycarbonyl (Cbz) protecting group on the amino functionality, while the aryl side chain bears an iodine substituent that provides a handle for halogen-based reactivity and spectroscopic or labeling applications. In peptide and amino acid synthesis, this protected derivative is used as a building block to introduce a phenylalanine-like residue bearing a para-iodo substituent, supporting structure-activity studies, conjugation strategies, and the preparation of more complex iodinated amino acid and peptide analogues.
CAT No: CP15209
Cbz-4-Iodo-D-Phenylalanine is a D-configuration phenylalanine derivative bearing a benzyloxycarbonyl (Cbz) carbamate on the amino group and an aryl iodide at the para position of the side-chain phenyl ring. The molecule therefore combines a chiral amino acid stereocenter with an electrophilic, halogenated aromatic handle that can participate in cross-coupling chemistry while remaining compatible with standard amino acid protection strategies. The Cbz group provides acid-stable N-protection for peptide coupling workflows and can be removed under hydrogenolysis conditions to reveal the free amino functionality when needed. The presence of the aryl iodide and the protected carboxyl functionality (as present in the supplied derivative form) supports downstream conversion into diversified aromatic analogs used in peptide, peptidomimetic, and medicinal chemistry intermediate preparation.
1. Peptide Synthesis
Cbz-4-Iodo-D-Phenylalanine is applied in peptide building workflows where orthogonal N-protection and a stable aromatic iodide enable incorporation of a para-iodophenylalanine residue into protected peptide chains. The Cbz-protected amino group supports peptide coupling chemistry while the D-stereochemistry allows stereodefined placement of the residue for studies requiring non-natural amino acid stereochemistry. The para-iodo substituent can be retained through peptide assembly and later transformed into aryl-linked motifs via cross-coupling, enabling post-assembly functionalization of peptide scaffolds. The resulting iodinated peptide intermediates are useful for generating structure-defined analog libraries and for producing peptide conjugation handles after deprotection and derivatization.
2. Peptidomimetics And SAR
Cbz-4-Iodo-D-Phenylalanine is utilized in peptidomimetic and SAR-oriented chemical design where an iodinated aromatic side chain functions as a tunable vector for aromatic substitution patterns. The protected amino acid framework supports controlled installation of the D-phenylalanine motif into constrained analogs, while the para-iodo group serves as a reactive handle for Suzuki, Sonogashira, or related coupling strategies to generate substituted aryl variants. The Cbz carbamate strategy helps maintain the chiral center and amino functionality during intermediate synthesis, with deprotection enabling further derivatization or coupling to heteroaryl fragments. Downstream use includes preparation of analog series for structure-activity relationship studies that rely on systematic side-chain modification while preserving stereochemical identity.
3. Chemical Biology Labeling
Cbz-4-Iodo-D-Phenylalanine is suitable for chemical biology workflows that require site-specific incorporation of an aromatic electrophile for subsequent tagging or affinity probe construction. The protected amino group enables incorporation into peptide-like constructs or probe precursors, while the para-iodo aryl moiety can be converted into bioconjugation-ready aromatic substituents through coupling chemistry prior to or after assembly. The D-configuration can be leveraged to modulate protease stability and recognition properties of peptide-based probes, supporting experiments that compare stereochemical variants. The compound thereby functions as a chiral amino acid derivative intermediate for generating labeled biomolecule fragments, probe scaffolds, and chemically defined conjugation partners.
4. Chiral Building Block Synthesis
Cbz-4-Iodo-D-Phenylalanine is employed as a chiral amino acid intermediate in synthetic organic chemistry where stereodefined phenylalanine derivatives are needed for enantioselective route design and downstream aromatic functionalization. The D-stereocenter provides a defined stereochemical input for constructing non-natural amino acid sequences, while the Cbz carbamate offers a removable protecting-group strategy compatible with many peptide coupling conditions. The para-iodo substituent enables late-stage diversification of the aromatic ring, allowing iterative synthesis of chiral building blocks that differ only in aryl substitution. The resulting intermediates can feed into fine chemical synthesis programs that require controlled stereochemistry alongside a functional aromatic handle for subsequent coupling or derivatization.
5. Pharmaceutical Intermediate Preparation
Cbz-4-Iodo-D-Phenylalanine is applied in pharmaceutical intermediate preparation where protected amino acid derivatives and halogenated aromatic handles support scalable synthesis of non-natural amino acid motifs. The Cbz-protected amino functionality supports controlled conversion into peptide-like intermediates or protected coupling partners, while the iodinated para-phenyl ring can be transformed into substituted aromatic groups used in medicinal chemistry programs. The stereochemical integrity of the D-phenylalanine framework can be carried through manufacturing steps to provide consistent chiral inputs for subsequent synthesis of analogs. The compound thus serves as a process-compatible intermediate for producing diversified aromatic amino acid derivatives and related scaffold components used in industrial fine chemical production.
6. Cross-Coupling Derivatization
Cbz-4-Iodo-D-Phenylalanine is utilized for cross-coupling derivatization strategies that convert the para-iodo aromatic group into substituted aryl or heteroaryl functionalities while maintaining the protected amino acid core. The aryl iodide provides a direct electrophilic site for coupling reactions, enabling formation of C-C or C-N linked aromatic motifs that can be carried forward into peptide building blocks or peptidomimetic scaffolds. The Cbz carbamate can remain intact during coupling to preserve the amino protection state, with later deprotection enabling further peptide coupling or conjugation steps. The resulting substituted derivatives broaden the accessible chemical space around a stereodefined D-phenylalanine motif, supporting both research intermediate generation and downstream synthetic methodology development.
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