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Bulk Supply (R)-N-Fmoc-4-Bromophenylalanine丨CAS 198545-76-5
(R)-N-Fmoc-4-Bromophenylalanine is a protected derivative of 4-bromophenylalanine featuring an R-configured chiral center and a 9-fluorenylmethoxycarbonyl (Fmoc) protecting group on the amino functionality. The Fmoc group is widely used in peptide synthesis for temporary amino protection, while the bromine substituent at the para position of the aromatic ring provides a potential site for further chemical modification. These features make this compound a useful building block for peptide research, medicinal chemistry, and specialized organic synthesis.
Chemical Identifiers
| InChI | InChI=1S/C24H20BrNO4/c25-16-11-9-15(10-12-16)13-22(23(27)28)26-24(29)30-14-21-19-7-3-1-5-17(19)18-6-2-4-8-20(18)21/h1-12,21-22H,13-14H2,(H,26,29)(H,27,28)/t22-/m1/s1 |
| InChI Key | TVBAVBWXRDHONF-JOCHJYFZSA-N |
| Smiles | C1=CC=C2C(=C1)C(C3=CC=CC=C32)COC(=O)N[C@H](CC4=CC=C(C=C4)Br)C(=O)O |
| EC No. | 692-742-2 |
| MDL No. | MFCD00273460 |
| PubChem CID | 7020431 |
Applications
Applications in Peptide Synthesis
(R)-N-Fmoc-4-Bromophenylalanine can be used as a protected amino acid building block in solid-phase peptide synthesis and related research workflows. The Fmoc group protects the amino functionality during peptide-chain assembly and can generally be removed under suitable basic conditions to allow subsequent coupling steps. Its R-configuration provides a defined stereochemical feature for researchers developing peptides containing non-standard amino acid residues.
Applications in Medicinal Chemistry
In medicinal chemistry, this compound can serve as an intermediate for preparing structurally diverse amino-acid-derived molecules. Its R-stereochemistry supports the synthesis of stereochemically specified compounds, while the para-brominated aromatic ring provides opportunities for further molecular modification. These characteristics may support analogue synthesis, structure–activity relationship studies, and exploratory drug discovery research.
Applications in Cross-Coupling Reactions
Applications in Chiral Building Block Development
(R)-N-Fmoc-4-Bromophenylalanine is relevant to synthesis projects requiring an Fmoc-protected amino acid with defined R-configuration and a modifiable aromatic side chain. The protecting group enables controlled amino-group deprotection during multistep synthesis, while the bromine substituent provides a potential handle for further derivatization. This combination may be valuable in developing specialized intermediates for pharmaceutical and fine chemical research.
