4-Bromo-D-Phenylalanine is a non-proteinogenic, D-configured phenylalanine analogue bearing a bromine substituent at the 4-position of the benzyl side chain, classifying it as a halogenated aromatic amino acid derivative. The molecule contains a free amino group and a free carboxyl group, while the para-bromo aromatic ring provides a chemically addressable handle that can participate in halogen-specific transformations or serve as a spectroscopic/labeling motif in structure-activity studies. As a substrate-like building block for peptide and peptidomimetic synthesis, it enables incorporation of a para-halogenated aromatic residue to probe conformational effects, electronic influences, and crosslinking or conjugation strategies that rely on the presence of the aryl bromide.
CAT No: CP11202
CAS No:62561-74-4
Synonyms/Alias:BOC-LYS-OHT-BUTYLAMINE;62559-79-9
4-Bromo-D-Phenylalanine is a D-configured, halogenated phenylalanine analog featuring a para-bromine substituent on the aromatic side chain. This non-proteinogenic amino acid building block is commonly used in peptide and peptidomimetic synthesis where aryl halogenation provides a distinct handle for downstream derivatization and structure-activity relationship studies. Its stereochemical definition supports incorporation into designed peptide sequences to probe stereochemical effects on conformation, recognition, and chemical reactivity.
1. Peptide Library Building
4-Bromo-D-Phenylalanine is used by peptide chemistry groups to construct D-amino-acid-containing peptide libraries and analog series, enabling systematic evaluation of how D-configuration and para-halogen substitution influence peptide properties. The para-bromine substituent is particularly useful for generating chemically distinct analogs from a shared scaffold, supporting structure-activity relationship workflows in custom peptide synthesis and medicinal chemistry lead optimization. Researchers commonly select this building block when they need a defined aromatic substitution pattern that can later be diversified while maintaining a consistent amino acid stereochemical identity within the sequence.
2. Peptidomimetic SAR Studies
4-Bromo-D-Phenylalanine supports medicinal chemistry and chemical biology programs that investigate aromatic electronics and steric effects through halogenated phenylalanine replacements. The para-bromine group provides a convenient, chemically addressable substituent for comparative studies across analog panels, including evaluation of how aryl substitution impacts physicochemical behavior and binding-site interactions in receptor/ligand discovery campaigns. Teams developing peptidomimetic scaffolds often use this compound as a standardized building block to ensure reproducible substitution patterns when mapping SAR trends across D-amino-acid variants.
3. Chemical Biology Derivatization
4-Bromo-D-Phenylalanine is frequently employed as an intermediate building block for later functionalization of aromatic bromides in chemical biology workflows. The aryl bromine can be leveraged to introduce additional substituents onto the phenyl ring during probe or conjugate construction, allowing researchers to tune labeling chemistry, affinity motifs, or physicochemical characteristics of peptide-derived reagents. This makes the compound useful for teams preparing modified peptides, affinity reagents, or chemical probes where a stable, defined aromatic handle is required before final assembly.
4. Halogen-Directed Synthesis
4-Bromo-D-Phenylalanine is used in pharmaceutical intermediate development and specialty chemical manufacturing when a halogenated chiral amino acid building block is needed to access aryl-substituted derivatives with controlled substitution patterns. Process and development chemists often value the D-stereochemical definition for maintaining stereochemical integrity through downstream transformations and for producing consistent intermediate sets for analog generation. In industrial R&D settings, the para-bromine functionality provides a practical entry point to diversify aromatic substitution on phenylalanine-derived fragments while keeping the amino acid core consistent across batches.
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