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China Made Fmoc-2-fluoro-D-phenylalanine丨CAS 198545-46-9
Fmoc-2-Fluoro-D-Phenylalanine (CAS 198545-46-9) is a protected fluorinated amino acid used in peptide synthesis, medicinal chemistry, and pharmaceutical research. It features a D-phenylalanine backbone with a fluorine atom at the ortho (2-) position of the aromatic ring and a 9-fluorenylmethoxycarbonyl (Fmoc) protecting group on the amino functionality. This structure combines defined stereochemistry, aromatic fluorination, and temporary amino-group protection, making it a useful building block for preparing modified peptides and specialized research compounds.
Chemical Identifiers
| InChI | InChI=1S/C24H20FNO4/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 | ARHOAMSIDCQWEW-JOCHJYFZSA-N |
| Smiles | C1=CC=C(C(=C1)C[C@H](C(=O)O)NC(=O)OCC2C3=CC=CC=C3C4=CC=CC=C24)F |
| EC No. | 974-318-1 |
| MDL No. | MFCD00672553 |
| PubChem CID | 7129815 |
Applications
Applications in Peptide and Amino Acid Chemistry
Fmoc-2-Fluoro-D-Phenylalanine is suitable for solid-phase peptide synthesis (SPPS) and other peptide assembly workflows that use Fmoc-protected amino acids. The Fmoc group protects the amino functionality during chain assembly and can generally be removed under basic conditions. Its D-configuration and ortho-fluorinated aromatic side chain enable researchers to introduce specific stereochemical and structural modifications into peptide sequences for studies of conformation, stability, and biological interactions.
Applications in Medicinal Chemistry Research
In medicinal chemistry, Fmoc-2-Fluoro-D-Phenylalanine serves as a building block for fluorinated peptide analogues and amino acid-derived research compounds. The ortho-fluoro substituent can affect the electronic characteristics and spatial arrangement of the aromatic side chain, potentially influencing molecular conformation, lipophilicity, metabolic behavior, and binding interactions. Researchers can use this compound to investigate structure–activity relationships and evaluate the impact of stereochemistry and positional fluorination on molecular properties.
Applications in Pharmaceutical Research
This compound supports research involving modified peptides, peptide-based candidates, and specialized fluorinated intermediates. Its Fmoc protection facilitates controlled incorporation into suitable synthetic routes, while the D-configuration provides an alternative stereochemical arrangement for exploring peptide behavior and resistance to enzymatic degradation. It may be used in laboratory-scale discovery programs to study how amino acid substitutions influence molecular recognition and biological activity.
Applications in Organic Synthesis
Fmoc-2-Fluoro-D-Phenylalanine can also function as an intermediate in multistep organic synthesis. Its protected amino group allows chemists to manage reaction selectivity, while the ortho-fluorinated aromatic ring provides a defined structural feature for further molecular design. The compound is relevant to the preparation of specialty amino acid derivatives, fluorinated peptides, and other research molecules requiring controlled stereochemistry and functional-group protection.
