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Procurement Fmoc-D-2-Bromophenylalanine丨CAS 220497-79-0
Fmoc-D-2-Bromophenylalanine is a protected non-natural amino acid used in peptide synthesis, medicinal chemistry, and specialized organic synthesis. It features a D-configured phenylalanine backbone, a bromine substituent at the 2-position of the aromatic ring, and a fluorenylmethoxycarbonyl (Fmoc) protecting group on the amino functionality. This combination of defined stereochemistry, an ortho-brominated aromatic side chain, and removable amino protection makes it a versatile building block for preparing modified peptides and structurally diverse research compounds.
Chemical Identifiers
| InChI | InChI=1S/C24H20BrNO4/c25-21-12-6-1-7-15(21)13-22(23(27)28)26-24(29)30-14-20-18-10-4-2-8-16(18)17-9-3-5-11-19(17)20/h1-12,20,22H,13-14H2,(H,26,29)(H,27,28)/t22-/m1/s1 |
| InChI Key | GRJPAUULVKPBHU-JOCHJYFZSA-N |
| Smiles | C1=CC=C(C(=C1)C[C@H](C(=O)O)NC(=O)OCC2C3=CC=CC=C3C4=CC=CC=C24)Br |
| EC No. | 852-970-7 |
| MDL No. | MFCD01311770 |
| PubChem CID | 7006559 |
Applications
Applications in Peptide Synthesis
Fmoc-D-2-Bromophenylalanine is suitable for use in solid-phase peptide synthesis (SPPS) and the preparation of peptide analogues containing D-amino acid residues. The Fmoc group protects the amino functionality during peptide-chain assembly and can be removed under suitable basic conditions to enable subsequent coupling steps. Incorporating its D-configuration and ortho-brominated aromatic side chain allows researchers to investigate how stereochemistry and side-chain modification influence peptide conformation, stability, and molecular interactions.
Applications in Medicinal Chemistry
In medicinal chemistry research, Fmoc-D-2-Bromophenylalanine can serve as an intermediate for preparing candidate compounds containing non-natural amino acid structures. The bromine substituent provides a potential site for further functionalization, including selected cross-coupling reactions under compatible conditions. Its defined D-configuration and protected amino group support multistep synthesis and the exploration of structure–activity relationships in peptide-based compounds and other research molecules.
Applications in Organic Synthesis
Applications in Non-Natural Amino Acid Research
Fmoc-D-2-Bromophenylalanine is relevant to research involving D-amino acids, non-proteinogenic amino acids, and structurally modified peptides. Its D-configuration provides a distinct spatial arrangement compared with the corresponding L-amino acid, while the ortho-bromine substituent alters the steric and electronic characteristics of the aromatic side chain. These features allow researchers to explore the relationship between amino acid configuration, peptide conformation, molecular recognition, and chemical reactivity.
