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Reliable Supplier (R)-N-Fmoc-3-Bromophenylalanine丨CAS 220497-81-4
(R)-N-Fmoc-3-Bromophenylalanine is a protected derivative of 3-bromophenylalanine featuring an R-configured chiral center and an N-terminal 9-fluorenylmethoxycarbonyl (Fmoc) protecting group. The Fmoc group is commonly used for temporary amino protection in peptide synthesis, while the bromine substituent at the 3-position of the aromatic ring provides a potential site for further chemical modification. These features make the compound a useful building block for peptide research, medicinal chemistry, and specialized 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-/m1/s1 |
| InChI Key | CALGTIKYXVBTAO-JOCHJYFZSA-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. | |
| MDL No. | MFCD01311771 |
| PubChem CID | 7006561 |
Applications
Applications in Peptide Synthesis
(R)-N-Fmoc-3-Bromophenylalanine can serve 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 enable subsequent coupling steps. Its R-configuration allows researchers to introduce a specific stereochemical feature into peptide sequences and investigate how amino acid configuration influences peptide properties.
Applications in Medicinal Chemistry
In medicinal chemistry, this compound can be used as an intermediate for preparing structurally diverse amino-acid-derived molecules. Its R-configured stereocenter supports the synthesis of stereochemically defined compounds, while the brominated aromatic ring offers opportunities for further functionalization. These features may support the preparation of molecular analogues for structure–activity relationship studies and exploratory drug discovery research.
Applications in Cross-Coupling Reactions
Applications in Chiral Building Block Development
(R)-N-Fmoc-3-Bromophenylalanine is relevant to synthesis projects requiring an Fmoc-protected amino acid with defined R-stereochemistry. The protecting group facilitates controlled amino-group deprotection during multistep synthesis, while the brominated aromatic side chain provides a handle for additional molecular modification. This combination can be useful in the preparation of specialized intermediates for peptide and pharmaceutical research.
