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Boc-L-4-Fluorophenylalanine丨CAS 41153-30-4 Manufacturer
Boc-L-4-Fluorophenylalanine (CAS 41153-30-4) is a protected, fluorinated amino acid used in peptide synthesis, medicinal chemistry, and pharmaceutical research. It consists of an L-phenylalanine 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/C14H18FNO4/c1-14(2,3)20-13(19)16-11(12(17)18)8-9-4-6-10(15)7-5-9/h4-7,11H,8H2,1-3H3,(H,16,19)(H,17,18)/t11-/m0/s1 |
| InChI Key | RCXSXRAUMLKRRL-NSHDSACASA-N |
| Smiles | CC(C)(C)OC(=O)N[C@@H](CC1=CC=C(C=C1)F)C(=O)O |
| EC No. | 671-834-6 |
| MDL No. | MFCD00079672 |
| PubChem CID | 7020910 |
Applications
Applications in Peptide Synthesis
Boc-L-4-Fluorophenylalanine is used as a protected amino acid building block in peptide synthesis. The Boc group helps prevent unwanted reactions at the amino group during peptide assembly and can be removed under suitable acidic conditions. Its L-configuration supports the preparation of stereochemically defined peptide sequences, while the para-fluorinated phenyl ring introduces a specific electronic modification that researchers can use to investigate peptide structure and function.
Applications in Medicinal Chemistry Research
In medicinal chemistry, Boc-L-4-Fluorophenylalanine serves as an intermediate for synthesizing fluorinated peptide analogues and other amino acid-derived compounds. Replacing a hydrogen atom with fluorine on the aromatic ring can influence electronic distribution, lipophilicity, metabolic stability, and molecular interactions. Researchers can use this building block to explore structure–activity relationships and assess how aromatic fluorination affects the properties of candidate molecules.
Applications in Pharmaceutical Research
Boc-L-4-Fluorophenylalanine supports research involving peptide-based compounds, modified amino acid sequences, and specialized pharmaceutical intermediates. Its protected amino group facilitates controlled incorporation into synthetic pathways, while its defined stereochemistry and fluorinated aromatic side chain offer opportunities to investigate changes in molecular recognition, stability, and biological activity. Its suitability depends on the target structure and the requirements of the research program.
Applications in Organic Synthesis
As a functionalized amino acid derivative, Boc-L-4-Fluorophenylalanine can be used in multistep organic synthesis to prepare more complex molecules containing a fluorinated aromatic amino acid unit. The Boc protecting group allows chemists to manage amino-group reactivity during synthesis and remove the protection when required. This makes the compound useful for research workflows involving specialty amino acid derivatives and structurally modified peptides.
