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3-Bromo-D-phenylalanine丨CAS 99295-78-0 Manufacturer
3-Bromo-D-phenylalanine is a halogenated derivative of D-phenylalanine, featuring a bromine substituent at the 3-position of the aromatic ring. Combining the D-configuration of the amino acid with a functionalized phenyl group, this compound is a useful building block for specialty organic synthesis, medicinal chemistry, and amino acid research. Its bromine substituent provides an opportunity for further chemical modification, while its stereochemistry supports the preparation of structurally defined compounds.
Chemical Identifiers
| InChI | InChI=1S/C9H10BrNO2/c10-7-3-1-2-6(4-7)5-8(11)9(12)13/h1-4,8H,5,11H2,(H,12,13)/t8-/m1/s1 |
| InChI Key | GDMOHOYNMWWBAU-MRVPVSSYSA-N |
| Smiles | C1=CC(=CC(=C1)Br)C[C@H](C(=O)O)N |
| EC No. | |
| MDL No. | MFCD06659100 |
| PubChem CID | 7047040 |
Applications
Applications in Peptide Synthesis
As a non-proteinogenic amino acid with D-configuration, 3-Bromo-D-phenylalanine may be incorporated into selected peptide research workflows where non-natural amino acid residues are required. The D-stereochemistry and brominated aromatic side chain provide structural variation for studying peptide conformation, molecular recognition, and the effects of amino acid modifications on peptide characteristics.
Applications in Medicinal Chemistry
3-Bromo-D-phenylalanine can be used as a specialized building block in medicinal chemistry research and the synthesis of amino-acid-derived compounds. Its aromatic bromine functionality offers a potential handle for further molecular modification, supporting the preparation of compound libraries and structural analogues for investigating molecular properties and structure–activity relationships.
Applications in Organic Synthesis
Applications in Chemical Biology
In chemical biology research, 3-Bromo-D-phenylalanine can support the design of non-natural amino acid structures for exploring interactions between peptides, proteins, and other molecular targets. Its distinct stereochemistry and aromatic substitution pattern allow researchers to investigate how structural changes influence molecular recognition and other properties in suitable experimental systems.
