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Fmoc-4-fluoro-L-phenylalanine丨CAS 169243-86-1 Manufacturer
Fmoc-4-Fluoro-L-Phenylalanine (CAS 169243-86-1) is a protected fluorinated amino acid widely used as a building block in peptide synthesis, medicinal chemistry, and pharmaceutical research. It contains an L-phenylalanine backbone with a fluorine substituent at the para (4-) position of the aromatic ring and a 9-fluorenylmethoxycarbonyl (Fmoc) protecting group on the amino functionality. This combination provides defined stereochemistry, aromatic fluorination, and temporary amino-group protection for controlled synthesis of peptides and specialized compounds.ine backbone with a fluorine atom at the para (4-) position of the aromatic ring and a tert-butoxycarbonyl (Boc) protecting group on the amino group. This structure makes it a valuable building block for preparing modified peptides and fluorinated compounds while providing temporary protection for the amino functionality during multistep synthesis.
Chemical Identifiers
| InChI | InChI=1S/C24H20FNO4/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-/m0/s1 |
| InChI Key | IXUMACXMEZBPJG-QFIPXVFZSA-N |
| Smiles | C1=CC=C2C(=C1)C(C3=CC=CC=C32)COC(=O)N[C@@H](CC4=CC=C(C=C4)F)C(=O)O |
| EC No. | 671-840-9 |
| MDL No. | MFCD00191197 |
| PubChem CID | 2734466 |
Applications
Applications in Peptide Synthesis
Fmoc-4-Fluoro-L-Phenylalanine is particularly suitable for solid-phase peptide synthesis (SPPS), where the Fmoc group protects the amino group during peptide-chain assembly. The protecting group can generally be removed under basic conditions, allowing sequential amino acid coupling while maintaining compatibility with many Fmoc-based synthesis workflows. Its L-configuration and para-fluorinated aromatic side chain enable researchers to introduce specific structural modifications into peptide sequences for peptide design and structure–activity relationship studies.
Applications in Medicinal Chemistry Research
In medicinal chemistry, Fmoc-4-Fluoro-L-Phenylalanine serves as a building block for preparing fluorinated peptides, amino acid derivatives, and other candidate molecules. Introducing fluorine at the para position can modify the electronic characteristics of the aromatic ring and may influence lipophilicity, metabolic stability, and molecular interactions. Researchers can use this compound to explore the relationship between structural changes and biological activity during compound optimization.
Applications in Pharmaceutical Research
This protected amino acid supports research involving peptide-based candidates, modified protein fragments, and synthetic amino acid sequences. The Fmoc group facilitates controlled incorporation into peptide chains, while the fluorinated phenyl ring offers an additional molecular feature for investigating conformation, binding behavior, and physicochemical properties. It is useful in laboratory-scale discovery and development workflows where stereochemical control and defined amino acid substitutions are important.
Applications in Organic Synthesis
Fmoc-4-Fluoro-L-Phenylalanine can also function as an intermediate in multistep organic synthesis. Its protected amino functionality allows chemists to manage reaction selectivity, while the fluorinated aromatic group can be retained as a structural element in more complex molecules. The compound is relevant to synthetic routes involving fluorinated amino acids, peptide intermediates, and specialty organic compounds.
