Cbz-4-Bromo-L-Phenylalanine is a Cbz-protected, L-phenylalanine-derived amino acid bearing a 4-bromo substituent on the aromatic side chain, placing it in the class of halogenated, protected amino acids used for peptide chemistry. The molecule contains a benzyl oxycarbonyl (Cbz) carbamate protecting the α-amino group while retaining the free carboxylic acid functionality, and the bromine substituent on the para position provides a distinct electrophilic/halogen handle for structure-activity studies and downstream derivatization. In synthesis, the protected amino acid is employed as a building block for stepwise peptide assembly and for preparing halogenated peptide analogues, while its aryl bromide functionality supports chemical labeling, conjugation strategies, and analytical method development involving halogenated aromatic residues.
CAT No: CP11208
Cbz-4-Bromo-L-Phenylalanine is an L-phenylalanine derivative bearing a benzyloxycarbonyl (Cbz) protecting group on the amino functionality and a para-bromine substituent on the aromatic side chain. The molecule contains a chiral α-carbon consistent with L-configuration, alongside a carboxylic acid functionality that can participate in peptide coupling after activation. The aryl bromide provides a defined electrophilic handle for cross-coupling and subsequent side-chain elaboration, while the Cbz group supports orthogonal protection strategies commonly used in peptide chemistry. The combination of a protected amino acid scaffold and a reactive aryl halide makes the compound suitable as a chiral intermediate for constructing brominated aromatic residues and downstream functionalized analogs.
1. Peptide Synthesis
Cbz-4-Bromo-L-Phenylalanine is applied in peptide building block preparation where the Cbz-protected amine enables controlled peptide coupling at the α-carboxyl group. The L-stereocenter preserves stereochemical integrity during amide bond formation, while the para-bromo substituent remains available for later diversification after incorporation into a growing peptide chain. Cbz protection is compatible with standard peptide coupling workflows and can be removed under hydrogenolysis conditions to expose the free amine for subsequent coupling steps. Brominated phenylalanine residues generated from this intermediate can be used to access peptide analogs for binding studies, labeling strategies, and structure-activity relationship (SAR) exploration in peptide science.
2. Side-Chain Functionalization
Cbz-4-Bromo-L-Phenylalanine is suitable for aromatic side-chain functionalization in synthetic organic chemistry and medicinal chemistry intermediate design. The aryl bromide at the 4-position can undergo palladium-catalyzed cross-coupling reactions to install aryl, heteroaryl, or substituted motifs while the amino acid backbone remains protected for chemoselective handling. The Cbz group helps maintain the amine as a stable protecting group during side-chain elaboration, enabling sequential transformations such as arylation followed by later deprotection and coupling. Resulting bromine-derived analogs can serve as intermediates for peptidomimetics, constrained aromatic scaffolds, and diversified amino acid derivatives used in SAR studies.
3. Chiral Building Block Development
Cbz-4-Bromo-L-Phenylalanine functions as a chiral amino acid intermediate for stereodefined synthesis of brominated phenylalanine-containing compounds. The L-configuration at the α-carbon supports predictable stereochemical outcomes in downstream peptide coupling and in the synthesis of chiral ligands, enzyme probes, and stereochemically defined fragments. The protected amino group (Cbz) provides a stable handle for protecting-group orthogonality, allowing the compound to be carried through multi-step sequences that include aromatic substitution and peptide assembly. The resulting chiral products can be employed as defined building blocks for fragment-based molecular design and for generating libraries of stereochemically consistent amino acid derivatives.
4. Bioconjugation Chemistry
Cbz-4-Bromo-L-Phenylalanine can be utilized in bioconjugation workflows where incorporation of a brominated aromatic residue supports later chemical diversification. The para-bromine handle can be converted into functional aromatic substituents that may improve conjugation chemistry, provide attachment points for linkers, or support affinity reagents used in chemical biology. Cbz protection allows the molecule to be processed as a protected amino acid precursor during synthesis of peptide-based conjugates, with deprotection enabling sequential assembly of conjugation-ready sequences. Downstream derivatives prepared from this intermediate can serve as defined components for labeling, targeted molecular probes, and biomolecule modification strategies that rely on precise side-chain architecture.
5. Pharmaceutical Manufacturing
Cbz-4-Bromo-L-Phenylalanine is relevant to pharmaceutical manufacturing routes that require controlled preparation of protected amino acid intermediates and halogenated aromatic residues. The Cbz-protected amine and carboxylic acid functionality allow the compound to be incorporated into peptide-like intermediates under standard coupling and protecting-group management practices used in fine chemical production. The stable aryl bromide can be retained through intermediate stages and transformed at a later manufacturing step to reach the desired substituted aromatic pattern for drug substance or drug-related intermediates. Process chemistry planning can leverage the orthogonality of Cbz protection with subsequent deprotection/coupling operations, supporting reliable generation of structurally defined chiral intermediates for scale-up.
6. Analytical Research Standards
Cbz-4-Bromo-L-Phenylalanine is suitable as an analytical reference material and method development intermediate for characterizing brominated phenylalanine-containing peptides and amino acid derivatives. The presence of the Cbz group and the para-bromine substituent provides distinct chromatographic and spectroscopic signatures that can aid in monitoring protection/deprotection steps, coupling efficiency, and side-chain transformation outcomes. The defined L-stereochemistry and protected functional groups support consistent analytical comparison across synthetic batches and during impurity profiling. Analytical workflows can employ derivatives derived from this intermediate to support LC-MS identification, structural confirmation, and stability studies of aromaticly substituted amino acid building blocks.
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