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L-2-Bromophenylalanine丨CAS 42538-40-9 Manufacturer
L-2-Bromophenylalanine is a non-natural amino acid featuring an L-configured phenylalanine backbone with a bromine substituent at the 2-position of the aromatic ring. Its defined stereochemistry and reactive halogen substituent make it a valuable building block for peptide synthesis, medicinal chemistry, and specialized organic synthesis. The bromine atom can provide a site for further functionalization in suitable chemical reactions, while the amino acid framework supports the preparation of structurally diverse compounds for research and development.
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-/m0/s1 |
| InChI Key | JFVLNTLXEZDFHW-QMMMGPOBSA-N |
| Smiles | C1=CC=C(C(=C1)C[C@@H](C(=O)O)N)Br |
| EC No. | 805-065-6 |
| MDL No. | MFCD05227934 |
| PubChem CID | 193338 |
Applications
Applications in Peptide Synthesis
L-2-Bromophenylalanine can be incorporated into synthetic peptides and peptide analogues to introduce a brominated aromatic side chain. This structural modification allows researchers to explore how halogen substitution affects peptide conformation, molecular interactions, and biological properties. With an appropriate amino-protecting group and coupling strategy, this amino acid can be used in peptide assembly and the preparation of non-natural peptide sequences.
Pharmaceutical and Medicinal Chemistry Research
As a specialized amino acid building block, L-2-Bromophenylalanine may support exploratory research involving amino acid derivatives, peptide-based compounds, and complex organic molecules. Its combination of a chiral amino acid scaffold and a reactive aromatic substituent provides flexibility in synthetic planning. Actual applications depend on the target structure, reaction conditions, and the compatibility of the bromine functionality with other components of the synthesis.
Applications in Organic Synthesis
Applications in Non-Natural Amino Acid Research
L-2-Bromophenylalanine is relevant to research focused on non-proteinogenic amino acids and the design of structurally modified peptides. Its L-configuration maintains a defined stereochemical arrangement, while the ortho-bromine substituent changes the steric and electronic characteristics of the phenyl ring. Researchers can use this combination to investigate the influence of side-chain modifications on molecular recognition, peptide structure, and chemical reactivity.
