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3-Bromo-L-phenylalanine丨CAS 82311-69-1 Supplier
3-Bromo-L-phenylalanine is a non-natural amino acid featuring an L-configured phenylalanine backbone with a bromine substituent at the 3-position of the aromatic ring. Its defined stereochemistry and brominated aromatic side chain make it a useful building block for peptide synthesis, medicinal chemistry, and specialized organic synthesis. The bromine substituent offers opportunities for further chemical functionalization, while the amino acid framework supports the development of structurally diverse molecules for research and development.
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-/m0/s1 |
| InChI Key | GDMOHOYNMWWBAU-QMMMGPOBSA-N |
| Smiles | C1=CC(=CC(=C1)Br)C[C@@H](C(=O)O)N |
| EC No. | 672-536-9 |
| MDL No. | MFCD06659110 |
| PubChem CID | 2762259 |
Applications
Applications in Peptide Synthesis
3-Bromo-L-phenylalanine can be incorporated into synthetic peptides and peptide analogues to introduce a brominated aromatic side chain. This structural modification allows researchers to explore how aromatic substitution influences peptide conformation, molecular interactions, and biological properties. With appropriate amino-group protection and coupling conditions, it can be used in the preparation of specialized peptide sequences and non-natural peptide building blocks.
Applications in Medicinal Chemistry
In medicinal chemistry research, 3-Bromo-L-phenylalanine can serve as a building block for synthesizing candidate molecules containing modified amino acid residues. The bromine substituent provides a potential site for further functionalization, including selected cross-coupling reactions under compatible conditions. These transformations support the preparation of structurally diverse compounds and compound libraries for investigating structure–activity relationships and molecular properties.
Applications in Organic Synthesis
Applications in Non-Natural Amino Acid Research
In chemical biology, 3-Bromo-L-phenylalanine may support the design and synthesis of modified amino-acid structures for studying molecular recognition and biological interactions. Its use depends on the research objective, the compatibility of the brominated residue with the intended system, and the methods selected for synthesis, characterization, and evaluation.
