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Best Quality (S)-N-Fmoc-3-Bromophenylalanine丨CAS 220497-48-3
(S)-N-Fmoc-3-Bromophenylalanine is a protected derivative of 3-bromophenylalanine featuring an S-configured chiral center and an N-terminal 9-fluorenylmethoxycarbonyl (Fmoc) protecting group. The Fmoc group is widely used for temporary amino protection in solid-phase peptide synthesis, while the bromine substituent at the 3-position of the aromatic ring provides a potential site for further chemical modification. These structural features make this compound a useful building block for peptide research, medicinal chemistry, and advanced organic synthesis.
Chemical Identifiers
| InChI | InChI=1S/C24H20BrNO4/c25-16-7-5-6-15(12-16)13-22(23(27)28)26-24(29)30-14-21-19-10-3-1-8-17(19)18-9-2-4-11-20(18)21/h1-12,21-22H,13-14H2,(H,26,29)(H,27,28)/t22-/m0/s1 |
| InChI Key | CALGTIKYXVBTAO-QFIPXVFZSA-N |
| Smiles | C1=CC=C2C(=C1)C(C3=CC=CC=C32)COC(=O)N[C@@H](CC4=CC(=CC=C4)Br)C(=O)O |
| EC No. | 856-133-7 |
| MDL No. | MFCD01311744 |
| PubChem CID | 2734448 |
Applications
Applications in Peptide Synthesis
(S)-N-Fmoc-3-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 typically be removed under suitable basic conditions, allowing subsequent coupling steps. Its defined stereochemistry and brominated aromatic side chain enable the preparation of peptides with specialized structural features.
Applications in Medicinal Chemistry
In medicinal chemistry, this compound can serve as an intermediate for synthesizing amino-acid-derived molecules and structurally diverse research compounds. The S-configuration supports stereochemically defined synthesis, while the brominated aromatic ring provides opportunities for further functionalization. These characteristics may help researchers prepare molecular analogues for structure–activity relationship studies and lead-optimization programs.
Applications in Cross-Coupling Reactions
Applications in Chiral Building Block Development
(S)-N-Fmoc-3-Bromophenylalanine is suitable for synthesis projects that require a protected amino acid with defined stereochemistry and a modifiable aromatic side chain. The Fmoc group supports controlled amino-group deprotection during multistep synthesis, while the S-configuration helps maintain the intended stereochemical identity of the target compound. It may therefore support the development of specialized intermediates for pharmaceutical and fine chemical research.
