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Supply Quality (S)-N-Boc-2-Bromophenylalanine丨CAS 261165-02-0
(S)-N-Boc-2-Bromophenylalanine is a protected non-natural amino acid used in peptide synthesis, medicinal chemistry, and specialized organic synthesis. It features an S-configured amino acid backbone, a bromine substituent at the 2-position of the aromatic ring, and a tert-butoxycarbonyl (Boc) protecting group on the amino functionality. This combination of defined stereochemistry, an ortho-brominated phenyl group, and temporary amino protection makes it a useful building block for preparing structurally diverse compounds through controlled synthetic routes.
Chemical Identifiers
| InChI | InChI=1S/C14H18BrNO4/c1-14(2,3)20-13(19)16-11(12(17)18)8-9-6-4-5-7-10(9)15/h4-7,11H,8H2,1-3H3,(H,16,19)(H,17,18)/t11-/m0/s1 |
| InChI Key | XDJSTMCSOXSTGZ-NSHDSACASA-N |
| Smiles | CC(C)(C)OC(=O)N[C@@H](CC1=CC=CC=C1Br)C(=O)O |
| EC No. | 863-147-7 |
| MDL No. | MFCD01317709 |
| PubChem CID | 2734475 |
Applications
Applications in Peptide Synthesis
(S)-N-Boc-2-Bromophenylalanine can be used as a protected amino acid building block in the preparation of synthetic peptides and peptide analogues. The Boc group helps prevent unwanted reactions at the amino functionality during intermediate synthesis and can be removed under suitable acidic conditions when required for subsequent coupling. Its S-configuration and ortho-brominated aromatic side chain allow researchers to introduce specific structural features into peptide sequences and explore their effects on conformation and molecular interactions.
Applications in Medicinal Chemistry
In medicinal chemistry research, (S)-N-Boc-2-Bromophenylalanine can serve as an intermediate for preparing candidate molecules containing non-natural amino acid residues. The bromine substituent provides a potential site for further functionalization, including selected cross-coupling reactions under compatible conditions. Its protected amino group supports multistep synthesis, while the ortho-substitution pattern offers a distinct structural feature for investigating structure–activity relationships.
Applications in Organic Synthesis
Applications in Non-Natural Amino Acid Research
(S)-N-Boc-2-Bromophenylalanine is relevant to research involving non-proteinogenic amino acids and modified peptide building blocks. Its defined stereochemistry supports the preparation of compounds with controlled three-dimensional structures, while the ortho-bromine substituent changes the steric and electronic characteristics of the aromatic side chain. These features may help researchers investigate relationships between amino acid structure, peptide conformation, molecular recognition, and chemical reactivity.
