Boc-3,5-Difluoro-D-Phenylalanine is a protected, non-natural amino acid derivative featuring a D-phenylalanine backbone with two fluorine atoms on the aromatic ring at the 3 and 5 positions. The α-amino group is protected as a Boc carbamate while the molecule retains a free carboxylic acid, and the fluorinated side chain provides altered electronic and steric characteristics relative to unsubstituted phenylalanine. As a stepwise peptide-synthesis building block, the Boc-protected amino functionality supports controlled coupling chemistry, and the difluorinated aromatic motif can be used in peptide or protein analog preparation for structure-activity studies, conformational probing, and analytical method development involving fluorine-containing residues.
CAT No: CP13104
CAS No:205445-52-9
Synonyms/Alias:205445-52-9;Boc-L-3,5-Difluorophenylalanine;BOC-PHE(3,5-DIF)-OH;BOC-PHE(3,5-F2)-OH;(S)-N-Boc-3,5-difluorophenylalanine;N-BOC-3,5-DIFLUORO-L-PHENYLALANINE;BOC-3,5-DIFLUORO-L-PHENYLALANINE;(2S)-3-(3,5-difluorophenyl)-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoic acid;N-BOC-L-3,5-DIFLUOROPHENYLALANINE;L-Phenylalanine, N-[(1,1-dimethylethoxy)carbonyl]-3,5-difluoro-;Boc-3,5-difluoro-D-phenylalanine;(S)-2-((tert-Butoxycarbonyl)amino)-3-(3,5-difluorophenyl)propanoic acid;3,5-DIFLUORO-L-PHENYLALANINE, N-BOC PROTECTED;BOC-L-3,5-DIFLUOROPHE;(2S)-2-[(tert-butoxycarbonyl)amino]-3-(3,5-difluorophenyl)propanoic acid;(2S)-2-[(tert-butoxycarbonyl)amino]-3-(3,5-difluorophenyl)propionic acid;N-((1,1-Dimethylethoxy)carbonyl)-3,5-difluoro-L-phenylalanine;N-[(1,1-Dimethylethoxy)carbonyl]-3,5-difluoro-L-phenylalanine;Boc-Phe(3,5-F?)-OH;N-(tert-butoxycarbonyl)-3,5-difluoro-L-phenylalanine;SCHEMBL1448035;DTXSID40942718;CZBNUDVCRKSYDG-NSHDSACASA-N;MFCD00797556;AKOS015889851;AC-9065;HY-W037441;PS-11016;DB-001153;N-Boc-L-3 pound not5-difluorophenylalanine;CS-0093741;N10805;EN300-3345894;AS-813/43497447;N-(tert-butoxycarbonyl)-3,5-difluorophenylalanine;Boc-Phe(3,5-F2)-OH, >=98.0% (HPLC);(S)-2-(Boc-amino)-3-(3,5-difluorophenyl)propionic acid;N-[tert-Butoxy(hydroxy)methylidene]-3,5-difluorophenylalanine;2-(S)-tert-butoxycarbonylamino-3-(3,5-difluorophenyl)propionic acid;(s)-2-((t-butoxycarbonyl)amino)-3-(3,5-difluorophenyl)-propanoic acid;3,5-Difluoro-D-phenylalanine, N-BOC protected (Boc-D-Phe(3,5-diF)-OH);(2S)-2-{[(tert-butoxy)carbonyl]amino}-3-(3,5-difluorophenyl)propanoic acid;(S)-2-(TERT-BUTOXYCARBONYLAMINO)-3-(3,5-DIFLUOROPHENYL)PROPANOIC ACID;606-578-6;
Boc-3,5-Difluoro-D-Phenylalanine is a D-configured, non-natural phenylalanine derivative bearing two fluorine atoms on the aromatic ring and an N-terminal Boc protecting group. This combination of stereochemistry and ring fluorination makes it a commonly used building block for incorporating conformationally and electronically modified amino-acid residues into peptides and peptidomimetics. In medicinal chemistry and peptide drug discovery programs, it is selected when fluorinated aromatic side chains are used to tune structure-activity relationships and to probe how subtle changes to aromatic electronics and sterics influence downstream properties.
1. Peptide Drug Discovery Building Block
Boc-3,5-Difluoro-D-Phenylalanine is used by peptide medicinal chemists to assemble D-amino-acid-containing sequences where enhanced control over backbone stereochemistry and aromatic side-chain electronics is required. The N-Boc protection supports routine peptide synthesis workflows, while the 3,5-difluoro substitution provides a fluorinated phenylalanine residue that is frequently incorporated into lead optimization libraries and SAR (structure-activity relationship) studies. Researchers value this residue for generating analog series in which the aromatic ring's electronic character and steric profile are systematically varied without changing the overall amino-acid scaffold.
2. Peptidomimetic And SAR Studies
Boc-3,5-Difluoro-D-Phenylalanine is applied in peptidomimetic design and SAR campaigns aimed at understanding how fluorination of aromatic side chains affects physicochemical behavior and structure-driven binding hypotheses. Medicinal chemistry teams use this building block to create analogs that incorporate a defined D-configuration at the residue level, supporting systematic comparisons between L- and D-architectures or between different fluorination patterns. The fluorine atoms also offer a convenient handle for downstream analytical characterization and for designing analogs that differ primarily at the aromatic ring, enabling clearer interpretation of structure-property trends.
3. Protected Amino Acid Intermediate Synthesis
Boc-3,5-Difluoro-D-Phenylalanine is also used as a protected amino-acid intermediate for preparing customized fluorinated amino-acid derivatives and peptide segments in research and specialty chemical manufacturing. Process chemists and custom synthesis groups rely on the Boc-protected form to manage chemoselectivity during downstream transformations, particularly when building larger, more complex fluorinated fragments for contract peptide manufacturing or internal library production. The D-stereochemical integrity and the presence of the difluorinated aromatic side chain make it a practical starting material when the target intermediate must preserve both stereochemical and substitution pattern fidelity through subsequent coupling steps.
1. The spatiotemporal control of signalling and trafficking of the GLP-1R
5. Autoinhibition and phosphorylation-induced activation of phospholipase C-γ isozymes
If you have any peptide synthesis requirement in mind, please do not hesitate to contact us at . We will endeavor to provide highly satisfying products and services.
Creative Peptides is a trusted CDMO partner specializing in high-quality peptide synthesis, conjugation, and manufacturing under strict cGMP compliance. With advanced technology platforms and a team of experienced scientists, we deliver tailored peptide solutions to support drug discovery, clinical development, and cosmetic innovation worldwide.
From custom peptide synthesis to complex peptide-drug conjugates, we provide flexible, end-to-end services designed to accelerate timelines and ensure regulatory excellence. Our commitment to quality, reliability, and innovation has made us a preferred partner across the pharmaceutical, biotechnology, and personal care industries.
Read More