DL-4-Bromophenylglycine is a brominated phenylglycine amino acid derivative featuring a benzyl side chain bearing a para-position bromine substituent and a glycine-like backbone with an amino group and a carboxyl group. The molecule exists as a racemic mixture (DL), with the aromatic bromine substituent providing a site for halogen-influenced reactivity and for incorporation into structure-activity and labeling studies, while the free amino and carboxyl functionalities enable salt formation and peptide-coupling chemistry. DL-4-Bromophenylglycine is used as a building block in peptide and peptidomimetic synthesis where a halogenated aromatic residue is required, and it can also serve as a substrate analogue in analytical method development and chemical biology workflows that probe aromatic halogen substitution effects.
CAT No: CP10001
DL-4-Bromophenylglycine is a phenylglycine amino acid derivative featuring a benzylamine backbone with a carboxylic acid functionality and a para-bromine substituent on the aromatic ring. The compound exists as a racemic (DL) mixture at the α-carbon, providing both stereochemical configurations for use in chiral synthesis workflows and comparative SAR studies. The aryl bromide enables electrophilic aromatic substitution and transition-metal-catalyzed cross-coupling chemistry, while the amino acid functional groups support conversion to protected amino acid derivatives, peptide coupling partners, and downstream heteroatom-containing analogs. The combination of an amino acid handle and a reactive aryl halide makes DL-4-bromophenylglycine a practical intermediate for building stereodefined and functionalized aromatic amino acid scaffolds.
1. Peptide Coupling Building Block
DL-4-Bromophenylglycine supports peptide synthesis workflows through its amino acid functionality, which can be converted into N-protected forms and activated as a coupling partner for amide bond formation. The para-bromophenyl side chain participates in protecting-group-stable peptide assembly, allowing incorporation into peptide sequences where aromatic electronics and halogen substitution influence conformational preferences and binding-site recognition. The racemic stereochemistry can be resolved or carried through as a defined mixture depending on the target library design, enabling parallel synthesis of diastereomeric or stereochemical variants after downstream chiral resolution. The resulting brominated peptide analogs can be further diversified by cross-coupling, providing a practical route from peptide construction to functionalized peptidomimetics.
2. Chiral Amino Acid Intermediate
DL-4-Bromophenylglycine serves as a chiral amino acid intermediate precursor because the α-carbon stereocenter is present in racemic form and can be separated into enantiopure derivatives when required. The aryl bromide withstands many standard amino acid protection and activation steps, enabling stereochemical control at the backbone while preserving a handle for later aromatic functionalization. N-protection strategies such as Boc, Cbz, or Fmoc-compatible variants can be applied to manage chemoselective coupling, while deprotection can reveal the free amine for subsequent transformations. Enantiopure downstream products can be used for stereodefined SAR studies, asymmetric synthesis planning, and preparation of chiral aromatic amino acid building blocks for peptide analog libraries.
3. Cross-Coupling Aromatic Diversification
DL-4-Bromophenylglycine is well suited for synthetic organic chemistry routes that leverage the para-bromine as a functional group for Pd-catalyzed coupling chemistry. The aryl bromide can be transformed into substituted biaryl, heteroaryl, or alkylated aromatic motifs, enabling systematic side-chain functionalization while retaining the amino acid core for further derivatization. Converting the carboxylic acid to an ester or protected acid derivative can improve compatibility with coupling conditions, followed by hydrolysis or deprotection to regenerate the amino acid functionality for peptide coupling or conjugation. The ability to introduce diverse aromatic substituents makes this intermediate useful for generating structure-diverse analog sets, including peptidomimetics and non-natural aromatic amino acid derivatives used in medicinal chemistry and chemical biology research.
4. Chemical Biology Labeling Handles
DL-4-Bromophenylglycine can be employed in chemical biology and biomolecule modification strategies where an amino acid scaffold is used to position an aromatic moiety for recognition or for linker attachment. The amino acid functionality supports conversion to protected derivatives for controlled coupling to peptide carriers, while the aryl bromide can serve as a chemical handle for installing additional substituents that tune hydrophobicity, electronics, or conjugation reactivity. Side-chain diversification through cross-coupling can introduce groups compatible with linker formation, affinity tags, or clickable motifs after appropriate protection of the amino and carboxyl groups. Racemic incorporation can be used for screening and mapping experiments where stereochemical effects are evaluated across analog series, supporting downstream generation of labeled peptide or protein-modified constructs.
5. Pharmaceutical Intermediate Preparation
DL-4-Bromophenylglycine fits pharmaceutical intermediate preparation workflows by providing a stable aromatic amino acid precursor that can be transformed into protected amino acid derivatives and stereochemically defined building blocks. The carboxylic acid and amino groups enable conversion into activated intermediates for amide coupling, while the para-bromine supports late-stage diversification toward substituted aromatic fragments common in drug-like scaffolds. Protection-group strategies allow selective manipulation of the N- and C-functionalities, supporting process chemistry routes that separate protection, coupling, and functionalization steps. The resulting brominated and cross-coupled amino acid derivatives can serve as intermediates for peptide-like drug candidates, peptidomimetics, and fine chemical synthesis where aromatic substitution patterns require controlled introduction.
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