D-4-Bromophenylglycine is a D-configured, non-proteinogenic amino acid derivative featuring a glycine backbone substituted with a 4-bromophenyl side chain, classifying it as a halogenated phenylglycine. The molecule contains a primary carboxylic acid and a primary amino group (as a free amino acid form unless otherwise specified) alongside a para-brominated aromatic ring that provides a distinct electrophilic/halogen handle for chemical derivatization and for tuning hydrophobic and steric properties in structure-activity studies. In peptide and amino acid chemistry workflows, it is used as a building block to introduce a brominated phenylglycine residue into peptide analogues and to support labeling, conjugation, or crosslinking strategies that rely on the presence of the aryl bromide functionality.
CAT No: CP10003
D-4-Bromophenylglycine is a D-configured amino acid in which the chiral center on the glycine backbone is adjacent to a para-brominated phenyl ring, providing a stereochemically defined aromatic side chain. The molecule contains a primary amino group and a carboxylic acid functionality that can participate in peptide coupling chemistry or be transformed into protected amino acid derivatives for controlled reactivity. The aryl bromide enables selective cross-coupling and electrophilic aromatic substitution strategies, while the D-stereochemistry supports stereodefined fragment assembly in chiral synthesis and structure-activity relationship studies. As an amino acid building block and chiral intermediate, D-4-Bromophenylglycine can be converted into protected forms, activated carboxylic acid derivatives, and downstream aryl-functionalized analogs used in synthetic organic chemistry and biochemical research workflows.
1. Peptide Synthesis
D-4-Bromophenylglycine is applied in peptide synthesis workflows where the amino acid backbone supports standard amide bond formation after appropriate N- and C-terminal activation. The presence of both an amino group and a carboxylic acid enables incorporation into peptide chains as a stereodefined D-amino acid residue, supporting the construction of D-amino acid-containing peptides and peptide fragments. The para-bromophenyl side chain can be retained through coupling steps when orthogonal protection is used, or it can be transformed after peptide assembly via aryl bromide chemistry. Downstream peptide analog preparation benefits from the ability to introduce a halogenated aromatic motif that can later be diversified for SAR studies and peptidomimetic scaffold generation.
2. Chiral Building Blocks
D-4-Bromophenylglycine serves as a chiral amino acid intermediate for stereoselective synthesis of enantiomerically defined aromatic glycine derivatives. The D-configuration at the amino acid stereocenter provides a fixed stereochemical handle for building chiral fragments used in medicinal chemistry and asymmetric synthesis planning. The carboxylic acid can be converted into protected amino acid derivatives or activated esters to enable controlled coupling, while the aryl bromide supports late-stage functionalization to introduce substituents without altering the stereochemical center. Chiral intermediate strategies using D-4-Bromophenylglycine can therefore support the preparation of stereodefined libraries for fragment-based molecular design and structure-activity relationship investigations.
3. Side-Chain Functionalization
D-4-Bromophenylglycine is utilized in side-chain functionalization chemistry where the para-brominated phenyl group functions as a reactive electrophile for cross-coupling and aryl diversification. The amino acid framework allows conversion to protected forms that maintain compatibility with coupling conditions, enabling sequential transformations such as halogen-to-aryl or halogen-to-heteroaryl substitution while preserving the D-stereocenter. The carboxyl functionality can be masked as an ester or protected acid derivative during coupling, then unmasked for subsequent derivatization or conjugation steps. Resulting aryl-modified amino acid analogs can feed downstream synthesis of peptidomimetics, enzyme-binding fragments, and chemical biology probes that require a stereochemically defined aromatic glycine motif.
4. Drug Discovery Intermediates
D-4-Bromophenylglycine is applied as a research intermediate in drug discovery programs focused on peptidomimetic and small-molecule fragment construction. The D-amino acid residue provides a stereodefined scaffold for incorporating nonproteinogenic character into bioactive candidates, while the para-bromophenyl motif supports modular diversification to explore chemical space. Functional group interconversion of the carboxylic acid and amino group enables preparation of coupling-ready derivatives for assembling larger structures, including amide-linked fragments and constrained analogs. Downstream use includes generating SAR-focused series and enabling systematic evaluation of how aryl substitution patterns and D-stereochemistry influence binding-relevant properties in medicinal chemistry campaigns.
5. Pharmaceutical Manufacturing Intermediates
D-4-Bromophenylglycine is suitable for industrial fine chemical synthesis routes that require a stereochemically defined halogenated amino acid intermediate. The amino acid's functional groups can be managed through standard protection and activation strategies to support scalable peptide-building-block preparation and controlled intermediate handling. The aryl bromide can be leveraged for manufacturing-compatible diversification steps that convert the brominated aromatic ring into substituted analogs used in downstream process chains. Industrial relevance also arises from the compound's role as a chiral starting material that can be carried through multi-step synthesis toward protected amino acid derivatives and final intermediate sets for pharmaceutical-grade chemical manufacturing workflows.
6. Analytical Standards And Labeling
D-4-Bromophenylglycine can be employed in analytical research as a stereochemically defined reference material for method development and impurity profiling of amino acid derivatives. The D-specific configuration and the para-brominated aromatic ring provide chromatographic and mass spectrometric distinguishability when monitoring protected amino acid intermediates, peptide fragments, or coupling byproducts. The presence of a reactive aryl bromide supports preparation of derivative standards through controlled functionalization, including conversion to alternative aryl substituents that serve as analytical comparators. Downstream analytical utility extends to supporting characterization workflows for chiral synthesis, peptide coupling chemistry, and amino acid derivatization processes where stereochemical integrity and aromatic substitution patterns must be verified.
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