3-Bromo-L-Phenylalanine is a naturally occurring amino acid derivative in which the aromatic side chain of L-phenylalanine is substituted at the meta position with a bromine atom, yielding a bromo-substituted phenylalanine suitable for incorporation as a modified aromatic building block. The molecule contains a free amino group and a free carboxyl group along with a benzyl-like aromatic ring bearing the bromine substituent, and its stereochemistry is specified as L at the alpha carbon. This halogenated amino acid is used in peptide synthesis and chemical biology workflows to introduce a site for halogen-specific reactivity, analytical differentiation, or structure-activity studies in peptides and related amino acid derivatives.
CAT No: CP11101
3-Bromo-L-Phenylalanine is an L-configured, halogenated phenylalanine building block featuring a benzyl bromide substituent on the aromatic ring. This electrophilic aryl bromide handle makes the residue particularly useful for downstream carbon-carbon and carbon-heteroatom bond-forming steps, while its amino acid functionality supports incorporation into peptide and peptidomimetic synthesis workflows. In chemical biology and medicinal chemistry programs, it is commonly selected when a site for selective derivatization or coupling is required without changing the stereochemical integrity of the amino acid backbone.
1. Peptide And Peptidomimetic Synthesis
3-Bromo-L-Phenylalanine is used as a halogenated amino acid building block for preparing modified peptides and peptidomimetics where an aryl bromide serves as a late-stage functionalization site. Researchers in peptide chemistry and medicinal chemistry incorporate the L-amino acid residue into custom sequences to enable subsequent diversification after assembly, supporting structure-activity relationship studies that require controlled variation of aromatic substituents. The presence of the stereodefined amino acid backbone allows chemists to maintain configurational fidelity while introducing an additional reactive handle on the aromatic ring.
2. Medicinal Chemistry Coupling Intermediate
3-Bromo-L-Phenylalanine is widely used in medicinal chemistry as an electrophilic aryl bromide intermediate for cross-coupling and derivatization strategies that build substituted aromatic systems around an amino acid core. Medicinal chemistry groups value this reagent when they need to append heterocycles, aryl groups, or other substituents to the phenyl ring after the amino acid has been incorporated into a larger scaffold or intermediate. The bromine substituent provides a practical platform for iterative library synthesis, enabling rapid generation of analogs while keeping the amino acid-derived stereochemical element consistent across a series.
3. Chemical Biology Probe And Tagging
3-Bromo-L-Phenylalanine supports chemical biology workflows that require an amino acid-based targeting motif combined with a chemically addressable aromatic handle for post-synthetic labeling. Chemical biology teams often use this building block to prepare modified peptide probes or amino acid-containing ligands that can be further coupled to affinity tags, reporter groups, or other functional moieties through bromide-reactive transformations. The aryl bromide functionality helps decouple probe assembly from final labeling, which is useful when downstream conjugation conditions must be tuned independently of peptide construction.
4. Analytical And Reference Material Development
3-Bromo-L-Phenylalanine is also used for analytical method development and reference material preparation in studies involving derivatized amino acid standards and amino acid-containing intermediates. Analytical chemistry laboratories use this compound to validate workflows that track halogenated amino acid motifs, support calibration of LC-MS or related quantification approaches, and enable characterization of derivatized products formed during synthesis or labeling experiments. Because the reagent retains an amino acid framework alongside a distinct brominated aromatic signature, it is a practical standard for confirming identity and monitoring transformations in complex chemical biology and medicinal chemistry pipelines.
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