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High Quality BOC-D-2-FluoroPhenylalanine丨CAS 114873-10-8
Boc-D-2-Fluorophenylalanine (CAS 114873-10-8) is a protected fluorinated amino acid used in peptide synthesis, medicinal chemistry, and organic synthesis. It features a D-phenylalanine backbone, a fluorine substituent at the ortho (2-) position of the aromatic ring, and a tert-butoxycarbonyl (Boc) protecting group on the amino functionality. Its defined stereochemistry and fluorinated aromatic structure make it a useful building block for preparing modified peptides and specialized research compounds.
Chemical Identifiers
| InChI | InChI=1S/C14H18FNO4/c1-14(2,3)20-13(19)16-11(12(17)18)8-9-6-4-5-7-10(9)15/h4-7,11H,8H2,1-3H3,(H,16,19)(H,17,18)/t11-/m1/s1 |
| InChI Key | NTWUXBKUDXGMHV-LLVKDONJSA-N |
| Smiles | CC(C)(C)OC(=O)N[C@H](CC1=CC=CC=C1F)C(=O)O |
| EC No. | 966-551-2 |
| MDL No. | MFCD00672521 |
| PubChem CID | 7020833 |
Applications
Applications in Peptide and Amino Acid Chemistry
Boc-D-2-Fluorophenylalanine serves as a protected amino acid building block for the synthesis of peptides and peptide analogues. The Boc group temporarily protects the amino functionality during peptide assembly and can be removed under suitable acidic conditions. Its D-configuration provides an alternative stereochemical arrangement to naturally occurring L-amino acids, while the ortho-fluorinated aromatic side chain allows researchers to explore changes in peptide conformation, stability, and interactions with biological targets.
Applications in Medicinal Chemistry Research
In medicinal chemistry, Boc-D-2-Fluorophenylalanine can be used to prepare fluorinated amino acid derivatives and structurally modified peptide candidates. The ortho-fluoro substituent can influence the electronic properties and spatial arrangement of the aromatic ring, potentially affecting molecular conformation, lipophilicity, metabolic behavior, and binding interactions. Researchers can use this building block in structure–activity relationship studies to investigate the effects of stereochemistry and fluorine substitution on compound properties.
Applications in Pharmaceutical Research
This compound supports research involving modified peptides, amino acid-derived intermediates, and candidate molecules containing fluorinated aromatic groups. Its protected amino group facilitates controlled incorporation into suitable synthetic routes, while its D-configuration allows researchers to investigate how stereochemical changes affect peptide behavior and biological activity. It is suitable for laboratory-scale research and compound development workflows in which defined stereochemistry and selective functional-group protection are important.
Applications in Organic Synthesis
Boc-D-2-Fluorophenylalanine can function as an intermediate in multistep organic synthesis for preparing more complex molecules containing an ortho-fluorinated amino acid unit. The Boc protecting group helps manage amino-group reactivity during synthesis and can be removed when required by the reaction sequence. This combination of stereochemical definition, aromatic fluorination, and temporary protection makes the compound useful for specialty amino acid chemistry and peptide-related synthesis.
