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Bulk Procurement D-4-bromophenylalanine丨CAS 62561-74-4
D-4-Bromophenylalanine is a non-proteinogenic amino acid featuring a D-configured amino acid backbone and a bromine substituent at the 4-position of the aromatic ring. Its defined stereochemistry and para-brominated phenyl group make it a valuable building block for peptide synthesis, medicinal chemistry, and specialized organic synthesis. The bromine substituent offers opportunities for further chemical modification, while the D-configuration provides an alternative stereochemical arrangement for designing modified peptides and structurally diverse research compounds.
Chemical Identifiers
| InChI | InChI=1S/C9H10BrNO2/c10-7-3-1-6(2-4-7)5-8(11)9(12)13/h1-4,8H,5,11H2,(H,12,13)/t8-/m1/s1 |
| InChI Key | PEMUHKUIQHFMTH-MRVPVSSYSA-N |
| Smiles | C1=CC(=CC=C1C[C@H](C(=O)O)N)Br |
| EC No. | 818-023-7 |
| MDL No. | MFCD01075126 |
| PubChem CID | 671215 |
Applications
Applications in Peptide Synthesis
D-4-Bromophenylalanine can be used to prepare synthetic peptides and peptide analogues containing D-amino acid residues. Incorporating this building block introduces a defined stereochemical configuration and a para-brominated aromatic side chain, enabling researchers to investigate how these features influence peptide conformation, stability, and molecular interactions. With suitable amino protection and coupling conditions, it can be incorporated into specialized peptide sequences for research and development.
Applications in Medicinal Chemistry
In medicinal chemistry, D-4-Bromophenylalanine serves as a building block for synthesizing candidate compounds containing non-natural amino acid structures. The para-bromine substituent provides a potential site for further functionalization, including selected cross-coupling reactions under compatible conditions. Combined with its D-configuration, this feature supports the exploration of molecular diversity and structure–activity relationships in peptide-based compounds and other synthetic molecules.
Applications in Organic Synthesis
Applications in Non-Natural Amino Acid Research
D-4-Bromophenylalanine is relevant to research involving D-amino acids and stereochemically modified peptides. The D-configuration changes the spatial arrangement of the amino acid backbone relative to its L-counterpart, while the para-bromine substituent provides a defined modification to the aromatic side chain. Researchers can use these structural features to investigate relationships between amino acid configuration, molecular recognition, peptide architecture, and chemical reactivity.
