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Bulk Procurement (S)-N-Boc-4-Bromophenylalanine丨CAS 62129-39-9
(S)-N-Boc-4-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 para-position of the phenyl ring, and a tert-butoxycarbonyl (Boc) protecting group on the amino functionality. This combination provides a versatile building block for controlled synthesis, enabling researchers to manage amino-group reactivity while introducing a brominated aromatic side chain into target molecules.
Chemical Identifiers
| InChI | InChI=1S/C14H18BrNO4/c1-14(2,3)20-13(19)16-11(12(17)18)8-9-4-6-10(15)7-5-9/h4-7,11H,8H2,1-3H3,(H,16,19)(H,17,18)/t11-/m0/s1 |
| InChI Key | ULNOXUAEIPUJMK-NSHDSACASA-N |
| Smiles | CC(C)(C)OC(=O)N[C@@H](CC1=CC=C(C=C1)Br)C(=O)O |
| EC No. | 834-866-3 |
| MDL No. | MFCD00237571 |
| PubChem CID | 2734477 |
Applications
Applications in Peptide Synthesis
(S)-N-Boc-4-Bromophenylalanine can serve as a protected amino acid building block for preparing peptides and peptide analogues. The Boc group temporarily protects the amino functionality during synthetic transformations and can be removed under suitable acidic conditions when a free amino group is required for subsequent coupling. Its defined stereochemistry and para-brominated aromatic side chain allow researchers to introduce specific structural features into peptide sequences and investigate their effects on conformation and molecular interactions.
Applications in Medicinal Chemistry
In medicinal chemistry research, (S)-N-Boc-4-Bromophenylalanine can be used as an intermediate for synthesizing candidate compounds containing modified amino acid residues. The bromine substituent provides a potential handle for further functionalization, including selected cross-coupling reactions under compatible conditions. Combined with the protected amino group, this functionality supports multistep synthesis and the exploration of structure–activity relationships in peptide-based and other small-molecule research programs.
Applications in Organic Synthesis
Applications in Non-Natural Amino Acid Research
(S)-N-Boc-4-Bromophenylalanine is relevant to research involving non-proteinogenic amino acids and structurally modified peptide building blocks. Its defined stereochemistry helps researchers plan the incorporation of a specific amino acid configuration, while the para-bromine substituent introduces a distinct aromatic modification. These structural features can support investigations into molecular recognition, peptide structure, and the influence of aromatic substitution on the properties of synthesized compounds.
