Boc-4-Bromo-D-Phenylalanine is a Boc-protected, non-natural amino acid derivative featuring a D-phenylalanine backbone with a para-bromo substituent on the phenyl side chain. The molecule contains a Boc-protected α-amino group and a free carboxyl group, while the aryl side chain bears a bromine substituent that can function as a chemically addressable handle for further derivatization. In peptide and amino acid chemistry, this protected analogue is used as a building block for controlled incorporation of a halogenated aromatic residue into synthetic peptides and for structure-activity or labeling studies where a bromo-substituted side chain is required.
CAT No: CP11205
CAS No:79561-82-3
Synonyms/Alias:79561-82-3;Boc-4-bromo-D-phenylalanine;Boc-D-4-Bromophenylalanine;(R)-N-Boc-4-bromophenylalanine;(R)-3-(4-Bromophenyl)-2-((tert-butoxycarbonyl)amino)propanoicacid;BOC-D-4-BROMOPHE;BOC-D-4-BR-PHE-OH;Boc-D-phe(4-Br)-OH;(2R)-3-(4-bromophenyl)-2-[(tert-butoxycarbonyl)amino]propanoicacid;N-(tert-Butoxycarbonyl)-4-bromo-D-phenylalanine;N-ALPHA-T-BUTYLOXYCARBONYL-D-4-BROMOPHENYLALANINE;BOC-(R)-2-AMINO-3-(4'-BROMOPHENYL)PROPANOICACID;(R)-3-(4-BROMO-PHENYL)-2-TERT-BUTOXYCARBONYLAMINO-PROPIONICACID;AC1ODSVE;PubChem23288;KSC495K8N;BOC-4'-BROMO-D-PHE;BOC-P-BROMO-D-PHE-OH;SCHEMBL763600;BOC-D-4-BROMO-PHE-OH;N-Boc-4-bromo-D-phenylalanine;CTK3J5586;MolPort-001-758-353;ULNOXUAEIPUJMK-LLVKDONJSA-N;ZINC2562492
Boc-4-Bromo-D-Phenylalanine is a D-configured phenylalanine derivative bearing a Boc-protected alpha-amino group and a 4-bromo substituent on the aromatic ring. This combination of stereochemical control, acid-stable Boc protection, and an aryl bromide functional handle makes it a practical building block for assembling modified peptides and for downstream medicinal chemistry diversification where halogenated aromatic motifs are required. Researchers commonly select this compound when they need a defined D-amino acid residue and a reactive aryl halide for subsequent coupling or late-stage functionalization.
1. D-Amino Acid Peptide Building Block
Boc-4-Bromo-D-Phenylalanine is used in custom peptide synthesis workflows to introduce a D-phenylalanine residue with a para-bromo aromatic substituent. Peptide chemists rely on the Boc-protected amino group to enable controlled coupling strategies during peptide assembly, while the D-stereochemistry supports the preparation of stereochemically defined peptide analogs used in structure-activity relationship studies and protease-related stability investigations. The aryl bromide also provides a convenient chemical "handle" for later diversification of the assembled peptide without changing the backbone stereochemical identity.
2. Halogenated Aromatic Intermediate Synthesis
Boc-4-Bromo-D-Phenylalanine serves as a stereodefined intermediate for medicinal chemistry and specialty chemical synthesis where a 4-bromophenylalanine motif is required. Process and R&D chemists use the preserved Boc-protected amino functionality as a protected precursor that can be carried through sequence steps, while the aryl bromide enables further transformations such as cross-coupling-based installation of aryl or heteroaryl substituents. This makes the reagent valuable for generating analog libraries in which aromatic substitution patterns are tuned around a chiral, D-amino acid core.
3. Peptide Diversification via Cross-Coupling
Boc-4-Bromo-D-Phenylalanine is frequently selected as a "functionalized residue" building block for preparing peptides or peptide fragments that can be diversified after assembly. By incorporating the para-bromo aromatic group early, downstream chemists can perform coupling-based substitution to introduce new aryl groups while retaining the D-amino acid configuration established during synthesis. This approach is particularly useful when the final substitution pattern is determined iteratively during lead optimization, enabling efficient generation of structure-defined analogs for chemical biology studies and SAR campaigns.
4. Chiral SAR Analog Preparation
Boc-4-Bromo-D-Phenylalanine supports the preparation of chiral, halogenated amino acid analogs used to probe how aromatic substitution and stereochemistry jointly influence molecular properties. Medicinal chemistry teams use this building block to construct D-amino acid-containing peptide mimetics or constrained fragments where the para-bromo group acts as a modular site for systematic variation. The defined stereochemistry and protected amino functionality help maintain batch-to-batch consistency in analog libraries, which is important for reproducible comparative evaluation in research settings.
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