Hangzhou Leap Chem Co., Ltd. is one of the most professional manufacturers and suppliers of (r)-n-boc-2-bromophenylalanine丨cas 261360-76-3 in China. Welcome to wholesale bulk high quality chemical products at competitive price from our factory. If you have any enquiry about custom service, please feel free to email us.
Supply Quality (R)-N-BOC-2-Bromophenylalanine丨CAS 261360-76-3
(R)-N-BOC-2-Bromophenylalanine is a protected non-natural amino acid used in peptide synthesis, medicinal chemistry, and specialized organic synthesis. It features an R-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. The combination of defined stereochemistry, an ortho-brominated phenyl group, and temporary amino protection makes this compound a useful building block for preparing structurally diverse molecules 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-/m1/s1 |
| InChI Key | XDJSTMCSOXSTGZ-LLVKDONJSA-N |
| Smiles | CC(C)(C)OC(=O)N[C@H](CC1=CC=CC=C1Br)C(=O)O |
| EC No. | 880-823-7 |
| MDL No. | MFCD01317703 |
| PubChem CID | 7006627 |
Applications
Applications in Peptide Synthesis
(R)-N-BOC-2-Bromophenylalanine can be used as a protected amino acid building block in the preparation of synthetic peptides and peptide analogues containing non-natural amino acid residues. The BOC group temporarily protects the amino functionality during synthesis and can be removed under suitable acidic conditions when a free amino group is required for subsequent coupling. Its R-configuration and ortho-brominated aromatic side chain allow researchers to introduce specific stereochemical and structural features into peptide sequences.
Applications in Medicinal Chemistry
In medicinal chemistry research, (R)-N-BOC-2-Bromophenylalanine can serve as an intermediate for preparing candidate molecules containing modified amino acid structures. The bromine substituent provides a potential site for further functionalization, including selected cross-coupling reactions under compatible conditions. Its defined R-configuration and protected amino group support the synthesis of structurally diverse compounds for investigating structure–activity relationships and molecular properties.
Applications in Organic Synthesis
Applications in Non-Natural Amino Acid Research
(R)-N-BOC-2-Bromophenylalanine is relevant to research involving non-proteinogenic amino acids and stereochemically modified peptides. Its R-configuration provides a defined spatial arrangement of the amino acid backbone, while the ortho-bromine substituent changes the steric and electronic characteristics of the aromatic side chain. These features allow researchers to explore how amino acid configuration and aromatic substitution influence peptide conformation, molecular recognition, and chemical reactivity.
