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Boc-L-3-Fluorophenylalanine丨CAS 114873-01-7
Boc-L-3-Fluorophenylalanine is a protected, fluorinated derivative of L-phenylalanine used in peptide synthesis, medicinal chemistry, and organic synthesis. It features a tert-butoxycarbonyl (Boc) protecting group on the amino functionality and a fluorine atom at the meta position of the aromatic ring. The Boc group helps control amino-group reactivity during multistep synthesis, while the fluorine substituent can influence the electronic properties and molecular interactions of the resulting compounds. Its defined L-configuration makes this compound a useful building block for modified peptides, fluorinated amino acid derivatives, and specialized research intermediates.
Chemical Identifiers
| InChI | InChI=1S/C14H18FNO4/c1-14(2,3)20-13(19)16-11(12(17)18)8-9-5-4-6-10(15)7-9/h4-7,11H,8H2,1-3H3,(H,16,19)(H,17,18)/t11-/m0/s1 |
| InChI Key | FPCCREICRYPTTL-NSHDSACASA-N |
| Smiles | CC(C)(C)OC(=O)N[C@@H](CC1=CC(=CC=C1)F)C(=O)O |
| EC No. | 601-331-9 |
| MDL No. | MFCD00672522 |
| PubChem CID | 2734492 |
Applications
Applications in Peptide Synthesis
Boc-L-3-Fluorophenylalanine can be incorporated into peptide synthesis strategies that use Boc-protected amino acids. The Boc group can be removed under suitable acidic conditions to expose the amino group for subsequent coupling steps, supporting controlled peptide assembly. The L-configuration enables the preparation of stereochemically defined peptides, while the meta-fluorinated aromatic side chain provides an additional structural feature for investigating peptide conformation, molecular recognition, and structure–activity relationships.
Applications in Medicinal Chemistry Research
Fluorinated amino acid derivatives are useful in medicinal chemistry because fluorine substitution can modify molecular electronics, lipophilicity, and metabolic behavior. Boc-L-3-Fluorophenylalanine provides a protected building block for introducing a meta-fluorinated phenylalanine residue into target molecules. Researchers can use it to prepare peptide analogues and other compounds for investigating how aromatic fluorination affects physicochemical properties and biological activity.
Applications in Protein and Biochemical Research
Boc-L-3-Fluorophenylalanine may support research involving nonstandard amino acids, peptide structure, and molecular interactions. Fluorine substitution can provide a way to investigate how relatively small changes to an aromatic side chain affect molecular behavior. After appropriate deprotection and incorporation into a target structure, derivatives prepared from this building block may be used in selected biochemical and analytical research workflows.
Applications in Organic Synthesis
The protected amino functionality and free carboxyl group of Boc-L-3-Fluorophenylalanine offer flexibility for multistep synthetic transformations. The Boc group can be retained or removed at an appropriate stage, while the carboxyl group can participate in esterification, amide formation, and peptide coupling reactions. The fluorinated aromatic ring remains a useful structural feature in the resulting intermediates, supporting the preparation of specialized amino acid derivatives and functionalized molecules.
