Cbz-3-Bromo-D-Phenylalanine is a Cbz-protected, non-natural amino acid derivative featuring a D-phenylalanine backbone bearing a bromine substituent at the 3-position of the aromatic ring. The molecule contains a carboxyl functional group masked as a protected amino acid (with the N-terminus carbobenzyloxy, Cbz) and an aromatic side chain that bears the bromo substituent, while the stereochemical configuration at the α-carbon is specified as D. In peptide and amino acid synthesis, the Cbz protecting group supports chemoselective handling of the amino functionality, and the aryl bromide provides a chemically addressable handle for incorporation into structure-activity studies, conjugation strategies, and subsequent derivatization of aromatic side-chain functionality.
CAT No: CP11109
Cbz-3-Bromo-D-Phenylalanine is a D-configuration benzyl-protected amino acid derivative bearing a side-chain aryl group and a bromine substituent at the 3-position relative to the amino acid backbone. The molecule contains a carbamate-protected amine (Cbz, benzyloxycarbonyl) and a free carboxylic acid functionality, enabling controlled peptide coupling after standard activation while suppressing undesired amine reactivity. The stereogenic center at the alpha carbon preserves D-chirality during downstream transformations, supporting stereodefined incorporation into peptide sequences and chiral SAR workflows. The aryl bromide provides a chemically addressable handle for cross-coupling or nucleophilic substitution chemistry, allowing conversion into diverse side-chain analogs without disturbing the backbone stereochemistry.
1. Peptide Synthesis
Cbz-3-Bromo-D-Phenylalanine is applied in peptide building workflows where protected amino acid chemistry and side-chain functional handles are required. The Cbz carbamate protects the N-terminus during coupling, while the carboxylic acid can be activated for amide bond formation using standard peptide coupling chemistries. The D-configuration at the alpha position supports stereochemically defined peptide construction, and the 3-bromo substituent can be retained for post-assembly diversification or transformed after fragment coupling. The resulting brominated peptide intermediates can be used to generate libraries of analogs for biochemical studies and to prepare structurally defined peptidomimetics from a single chiral precursor.
2. Side-Chain Functionalization
Cbz-3-Bromo-D-Phenylalanine is utilized for side-chain functionalization strategies that convert an aryl bromide into new substituents while maintaining the amino acid scaffold. The bromine substituent on the phenyl ring serves as a reactive electrophile for Suzuki-Miyaura coupling, Buchwald-Hartwig amination, or related C-X substitution pathways, enabling installation of aryl, heteroaryl, or amino-functional groups. The Cbz-protected amine and carboxylic acid allow orthogonal protection planning, where side-chain modification can be performed under conditions compatible with the protected amino acid framework or after selective deprotection and re-protection. Downstream products include bromide-to-aryl/heteroaryl substituted phenylalanine derivatives that feed into SAR studies, chemical biology probes, and peptide analog construction.
3. Chiral Building Block Synthesis
Cbz-3-Bromo-D-Phenylalanine is suitable for chiral amino acid intermediate preparation in synthetic organic chemistry where stereochemical integrity is a key design constraint. The D-configuration at the alpha carbon provides a defined stereocenter for downstream incorporation into peptide sequences, enzyme substrate analogs, or chiral fragment assemblies. The Cbz group functions as a removable protecting group that can be managed to control whether the molecule behaves as an N-protected amino acid during coupling or as a free amine for further derivatization. The combination of a stable N-protection strategy and a brominated aromatic handle supports iterative synthesis of stereodefined derivatives used in method development and chiral scaffold generation.
4. Chemical Biology Probes
Cbz-3-Bromo-D-Phenylalanine is applied in chemical biology research to construct labeled or reactive peptide-like probes that contain a programmable aromatic electrophile. The brominated phenyl side chain can be leveraged for subsequent conjugation chemistry after incorporation into peptides or peptidomimetics, supporting workflows where a reactive handle is introduced at a defined stereochemical position. The Cbz-protected amine enables controlled peptide coupling to generate probe precursors without premature amide formation or side reactions. The D-amino acid stereochemistry can be used to tune protease resistance profiles of peptide analogs during probe synthesis, supporting studies that require non-natural amino acid incorporation. Resulting derivatives can be used as intermediates for affinity reagents, mechanistic probes, and structure-defined biomolecular interaction studies.
5. Pharmaceutical Intermediate Preparation
Cbz-3-Bromo-D-Phenylalanine is used as a process-relevant pharmaceutical intermediate for the synthesis of non-natural amino acid motifs and halogenated side-chain analogs. The protected amino acid format, featuring a Cbz-protected amine and a carboxylic acid, supports manufacturing-compatible conversion into activated coupling partners and subsequent assembly into peptidic or peptidomimetic intermediates. The aryl bromide enables late-stage diversification to introduce substituents commonly used in medicinal chemistry, including aryl/heteroaryl groups and nitrogen-containing functionalities, while preserving the D-chiral backbone. The stereodefined nature of the intermediate supports consistent scaffold generation across synthesis campaigns, and the brominated handle provides a controlled branching point for downstream synthetic routes. This makes the compound applicable to fine chemical synthesis and specialty chemical production where chiral, functionalized amino acid building blocks are required.
2. Emu oil in combination with other active ingredients for treating skin imperfections
4. SERS spectrum of the peptide thymosin‐β4 obtained with Ag nanorod substrate
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