Boc-4-Fluoro-D-Phenylalanine is a protected, non-natural amino acid derivative in which the amino group of 4-fluoro-D-phenylalanine is masked as a Boc (tert-butoxycarbonyl) carbamate and the side chain bears a para-fluorine substituent on the phenyl ring. The molecule contains a free carboxylic acid functionality and a Boc-protected amine, with stereochemistry specified as D at the alpha carbon, and the fluorinated aromatic side chain provides a defined electronic and steric environment for structure-activity and labeling studies. In peptide and amino-acid derivative synthesis, this protected analogue is used as a building block to control chemoselectivity of the amine during stepwise coupling while introducing the 4-fluoro phenyl motif into peptides, analogues, or other fluorinated conjugates.
CAT No: CP14605
CAS No:57292-45-2
Synonyms/Alias:57292-44-1;Boc-D-Phe(4-Cl)-OH;Boc-4-chloro-D-phenylalanine;Boc-D-4-Chlorophe;N-(tert-Butoxycarbonyl)-4-chloro-D-phenylalanine;Boc-D-4-Chlorophenylalanine;(R)-2-((tert-butoxycarbonyl)amino)-3-(4-chlorophenyl)propanoicacid;(R)-N-BOC-4-CHLOROPHENYLALANINE;N-Boc-4-chloro-D-phenylalanine;MFCD00076978;(2R)-2-[(tert-butoxycarbonyl)amino]-3-(4-chlorophenyl)propanoicacid;(2R)-2-(tert-butoxycarbonylamino)-3-(4-chlorophenyl)propanoate;PubChem12665;KSC911S3N;15471_ALDRICH;BOC-P-CHLORO-D-PHE-OH;SCHEMBL1309909;BOC-4-CHLORO-D-PHE-OH;BOC-D-4-CHLORO-PHE-OH;15471_FLUKA;CTK8B1936;BETBOAZCLSJOBQ-LLVKDONJSA-N;MolPort-002-343-976;ZINC2555043;BOC-P-CHLORO-D-PHENYLALANINE
Boc-4-Fluoro-D-Phenylalanine is a D-configured phenylalanine derivative bearing a 4-fluoro substituent on the aromatic ring and an N-terminal Boc protecting group, making it a stable, bench-ready building block for peptide and peptidomimetic synthesis. Its fluorinated side-chain provides a handle for medicinal chemistry programs that require aryl fluorine for electronic tuning and physicochemical property modulation, while the Boc group supports protected amino acid coupling workflows. In research settings, this reagent is commonly selected when a defined stereochemistry and a protected amine are required to introduce a fluorinated aromatic residue into larger peptide structures.
1. Fluorinated Peptide Building Block
Boc-4-Fluoro-D-Phenylalanine is used in custom peptide synthesis and peptide library construction to incorporate a D-configuration fluorinated phenylalanine residue at a defined position. Peptide chemists rely on the Boc-protected amine to maintain compatibility with protected-amino-acid assembly strategies, enabling controlled incorporation during segment coupling or stepwise synthesis. The 4-fluoro aromatic substitution is particularly valuable for generating fluorinated peptide analogs used in structure-activity relationship (SAR) studies, where subtle changes in electronics, hydrogen-bonding patterns, and metabolic stability proxies are investigated through systematic residue variation.
2. Peptidomimetic SAR Development
Boc-4-Fluoro-D-Phenylalanine supports medicinal chemistry and peptidomimetic development efforts that require fluorinated aromatic moieties to tune molecular properties without changing the overall peptide backbone composition. Researchers use this building block to prepare analog series where aryl fluorine placement and stereochemical configuration are controlled, allowing direct comparison of how fluorinated D-amino acid incorporation affects conformational preferences and physicochemical behavior in downstream assays. Because the reagent is already protected at the N-terminus, it fits efficiently into workflows that generate intermediate peptide fragments for later coupling, derivatization, or conversion into non-peptidic mimetics.
3. Protected Intermediate For Analog Synthesis
Boc-4-Fluoro-D-Phenylalanine is frequently handled as a pharmaceutical intermediate building block for generating fluorinated amino acid derivatives and peptide fragments used in lead optimization campaigns. Process and synthesis teams value the combination of a protected amine (Boc) and a stable aryl fluorine substituent for preparing well-defined intermediates that can be carried through multi-step assembly, purification, and characterization. This product is also used in analytical reference material preparation for fluorinated peptide analogs, where consistent stereochemistry and substitution pattern are essential for method development and comparative studies across compound series.
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