DL-4-Fluorophenylglycine is a non-proteinogenic, aromatic amino acid derivative featuring a benzyl side chain bearing a fluorine substituent at the para (4-) position relative to the alpha carbon, with the amino acid backbone containing both an amino group and a carboxylic acid. The molecule is supplied as the DL racemate, and its side chain bears a fluorinated phenyl ring that can influence hydrophobicity and electronic properties while remaining compatible with standard amino acid handling in peptide chemistry. DL-4-Fluorophenylglycine is used as a building block for incorporating fluorinated aromatic residues into peptides and peptide-like structures for structure-activity studies, chemical biology labeling strategies, and analytical method development where the presence of a fluorinated phenyl group provides a distinct spectroscopic or chemical handle.
CAT No: CP10201
DL-4-Fluorophenylglycine is a fluorinated phenylglycine amino acid derivative with a chiral center at the alpha carbon and a side chain bearing a para-fluorinated phenyl ring. The molecule contains an amino functionality and a carboxylic acid (or corresponding salt form depending on handling), enabling standard amino-acid coupling chemistry while the aromatic C-F bond provides distinctive electronic and steric features for medicinal chemistry and structure-based design. The DL stereochemical designation indicates a racemic mixture of enantiomers, which is relevant for screening, method development, and downstream resolution strategies. The aryl fluoride can participate in nucleophilic aromatic substitution under appropriate conditions or serve as a chemically stable handle for later derivatization, while the amino acid backbone supports conversion to protected building blocks and peptide-compatible intermediates.
1. Peptide Coupling Building Block
DL-4-Fluorophenylglycine is used in peptide synthesis research and fine chemical production as an amino acid building block for incorporating a fluorinated aryl side chain into peptide sequences. The amino acid backbone supports amide bond formation via conventional coupling strategies, while the para-fluorophenyl group can modulate local hydrophobicity and electronic character of the resulting peptide or peptidomimetic. Racemic incorporation may be applied for library generation, method scouting, or when stereochemical assignment occurs at a later stage through chiral resolution or asymmetric downstream transformations. Subsequent deprotection and side-chain retention of the aryl fluoride enable preparation of fluorinated peptide analogs suitable for SAR studies and analytical method development.
2. Peptidomimetics And SAR Studies
DL-4-Fluorophenylglycine is applied in peptidomimetic construction and structure-activity relationship studies where an aromatic fluorine substituent is used to tune binding interactions and metabolic stability proxies. The para-fluoro substituent provides a defined substituent pattern on the phenyl ring, supporting systematic variation of electronic effects across analog series while the glycine-like backbone allows incorporation into constrained or flexible scaffolds. The amino and carboxyl functionalities can be transformed into protected intermediates for controlled coupling, enabling consistent scaffold assembly for SAR panels. Downstream derivatization of the aryl fluoride, when desired, can generate additional analogs for receptor probing, fragment linking, or conformational studies within medicinal chemistry workflows.
3. Chiral Resolution Intermediate
DL-4-Fluorophenylglycine serves as a chiral synthesis feedstock for producing enantiopure fluorinated amino acid derivatives through resolution or stereoselective conversion strategies. The alpha-chiral center and the chemically robust aryl fluoride create a stereochemically informative substrate for forming diastereomeric salts or derivatives that can be separated, after which the purified enantiomer can be carried into protected amino acid synthesis. The amino acid functional groups support conversion to N-protected forms and activation of the carboxyl group to generate peptide coupling-ready intermediates. Enantiopure downstream products can then be used for stereochemically defined peptide building block preparation, chiral SAR libraries, and method development in synthetic organic chemistry.
4. Amino Acid Derivatization Chemistry
DL-4-Fluorophenylglycine is utilized in amino acid derivatization workflows to access fluorinated intermediates for medicinal chemistry and industrial intermediate preparation. The carboxylic acid and amino group enable formation of esters, amides, and N-protected derivatives that are compatible with stepwise synthesis, while the aromatic C-F bond can remain intact through multiple protection/deprotection cycles or be selectively functionalized when a substitution handle is required. Derivatization can support generation of labeled or tagged analogs for biochemical research, as well as conversion into activated species for subsequent coupling into larger molecules. The resulting fluorinated amino acid derivatives provide a practical platform for building heteroaryl-containing fragments, preparing substitution products, and expanding chemical space in applied synthesis programs.
5. Pharmaceutical Intermediate Preparation
DL-4-Fluorophenylglycine is relevant to pharmaceutical intermediate preparation and process chemistry development due to its stable fluorinated aromatic side chain and amino acid functionality that can be routed into protected building blocks. The molecule can be converted into N-protected amino acid derivatives and carboxyl-activated intermediates used for constructing amide-containing drug-like scaffolds, including fluorinated phenylglycine motifs within larger synthetic routes. The racemic starting material can be handled for early-stage manufacturing development, with stereochemical refinement introduced via resolution or downstream asymmetric steps depending on target requirements. The aryl fluoride can function as a persistent structural element during manufacturing sequence design or as a late-stage diversification site to access multiple analogs from a common intermediate.
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