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D-2-Bromophenylalanine丨CAS 267225-27-4 Supplier in China
D-2-Bromophenylalanine is a non-proteinogenic amino acid featuring a D-configured amino acid backbone and a bromine substituent at the 2-position of the aromatic ring. Its distinctive stereochemistry and halogenated side chain make it a useful building block for peptide chemistry, medicinal chemistry, and specialized organic synthesis. The bromine atom offers opportunities for further chemical modification, while the D-configuration provides an alternative stereochemical arrangement for designing modified peptides and other research compounds.
Chemical Identifiers
| InChI | InChI=1S/C9H10BrNO2/c10-7-4-2-1-3-6(7)5-8(11)9(12)13/h1-4,8H,5,11H2,(H,12,13)/t8-/m1/s1 |
| InChI Key | JFVLNTLXEZDFHW-MRVPVSSYSA-N |
| Smiles | C1=CC=C(C(=C1)C[C@H](C(=O)O)N)Br |
| EC No. | 898-279-4 |
| MDL No. | MFCD03092959 |
| PubChem CID | 7023575 |
Applications
Applications in Peptide Synthesis
D-2-Bromophenylalanine can be used in the preparation of synthetic peptides and peptide analogues containing D-amino acid residues. Incorporating this building block introduces both a defined stereochemical configuration and an ortho-brominated aromatic side chain, allowing researchers to investigate their effects on peptide conformation, stability, and molecular interactions. With suitable amino protection and coupling conditions, it can be incorporated into specialized peptide sequences for research purposes.
Applications in Medicinal Chemistry
In medicinal chemistry, D-2-Bromophenylalanine can serve as a building block for synthesizing candidate compounds containing non-natural amino acid structures. The 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 structural diversity and structure–activity relationships in peptide-based compounds and other molecular designs.
Applications in Organic Synthesis
Applications in Non-Natural Amino Acid Research
D-2-Bromophenylalanine is relevant to research involving non-natural 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 ortho-bromine substituent influences the steric and electronic characteristics of the aromatic side chain. Researchers can use these structural features to investigate relationships between amino acid configuration, molecular recognition, peptide architecture, and chemical reactivity.
