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Bulk Supply Boc-3-fluoro-D-phenylalanine丨CAS 114873-11-9
Boc-3-Fluoro-D-Phenylalanine (CAS 114873-11-9) is a protected, fluorinated D-amino acid used as a specialized building block in peptide chemistry and organic synthesis. It features a tert-butoxycarbonyl (Boc) protecting group on the amino group, a D-configuration at the alpha carbon, and a fluorine substituent at the 3-position of the phenyl ring. This combination provides researchers with a useful structural unit for preparing modified peptides and developing compounds with tailored chemical and biological properties.
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-/m1/s1 |
| InChI Key | FPCCREICRYPTTL-LLVKDONJSA-N |
| Smiles | CC(C)(C)OC(=O)N[C@H](CC1=CC(=CC=C1)F)C(=O)O |
| EC No. | 670-961-4 |
| MDL No. | MFCD00672523 |
| PubChem CID | 7020836 |
Applications
Applications in Peptide Synthesis
Boc-3-Fluoro-D-Phenylalanine is used in peptide synthesis as a protected amino acid building block. The Boc group temporarily protects the amino functionality during peptide assembly and can be removed under suitable acidic conditions. Its D-configuration and aromatic fluorine substitution enable researchers to introduce specific stereochemical and electronic features into peptide sequences, supporting the preparation of modified peptides for research and development.
Applications in Medicinal Chemistry Research
In medicinal chemistry, this compound can serve as an intermediate in the synthesis of fluorinated peptide analogues and other biologically relevant molecules. Incorporating fluorine into an aromatic ring can influence molecular properties such as electronic distribution, lipophilicity, metabolic stability, and binding interactions. The actual effects depend on the overall molecular structure and should be evaluated through experimental studies.
Applications in Pharmaceutical Research
Boc-3-Fluoro-D-Phenylalanine may be used in early-stage pharmaceutical research to prepare candidate compounds for structure–activity relationship studies. Its protected amino acid framework allows researchers to explore the effects of D-amino acid incorporation and aromatic fluorination on peptide conformation, stability, and biological activity. It can also support the synthesis of specialized intermediates for laboratory-scale drug discovery programs.
Applications in Organic Synthesis
Beyond peptide assembly, this compound can function as a versatile intermediate in multistep organic synthesis. The protected amino group and substituted aromatic ring provide opportunities for further transformations after appropriate deprotection or reaction design. It is suitable for research workflows that require stereochemically defined, fluorinated amino acid derivatives.
