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Supply High Quality Fmoc-L-2-bromophenylalanine丨CAS 220497-47-2
Fmoc-L-2-Bromophenylalanine is a protected non-natural amino acid used in peptide synthesis, medicinal chemistry, and specialized organic synthesis. It features an L-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-/m0/s1 |
| InChI Key | GRJPAUULVKPBHU-QFIPXVFZSA-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. | 635-226-4 |
| MDL No. | MFCD01311743 |
| PubChem CID | 2734447 |
Applications
Applications in Peptide Synthesis
Fmoc-L-2-Bromophenylalanine is particularly useful in solid-phase peptide synthesis (SPPS), where the Fmoc group protects the amino functionality during peptide-chain assembly. Under suitable basic conditions, the Fmoc group can be removed to enable subsequent coupling steps. Its L-configuration and ortho-brominated aromatic side chain allow researchers to introduce non-natural structural features into peptide sequences and investigate their influence on peptide conformation, stability, and molecular interactions.
Applications in Medicinal Chemistry
In medicinal chemistry research, Fmoc-L-2-Bromophenylalanine can serve as an intermediate for preparing peptide-based candidates and other compounds containing modified amino acid residues. The bromine substituent provides a potential site for further functionalization, including selected cross-coupling reactions under compatible conditions. These transformations can support compound library development and structure–activity relationship studies, helping researchers explore how aromatic substitution influences molecular properties and biological activity.
Applications in Organic Synthesis
Applications in Non-Natural Amino Acid Research
Fmoc-L-2-Bromophenylalanine is relevant to research involving non-proteinogenic amino acids and modified peptide building blocks. Its defined L-stereochemistry supports controlled incorporation into designed sequences, while the ortho-bromine substituent alters the steric and electronic characteristics of the aromatic side chain. Researchers can use this structural combination to investigate relationships between amino acid structure, peptide conformation, molecular recognition, and chemical reactivity.
