D-4-Fluorophenylglycine is a non-proteinogenic, aromatic amino acid derivative in which a glycine backbone bears a 4-fluorophenyl side chain, classifying it as a phenylglycine analogue with a fluorinated aromatic substituent. The molecule contains an amino group and a carboxyl group (free or present as the corresponding ionic form depending on the supplied material) and is specified in the D stereochemical configuration at the α-carbon, while the para-fluorine substituent modulates the aryl ring's electronic character and provides a distinct handle for chemical characterization and derivatization. It is used in peptide and structure-activity studies to introduce a fluorinated phenylglycine residue for probing conformational effects, aromatic interactions, and labeling or analytical detectability in chemical biology and synthetic peptide workflows.
CAT No: CP10203
D-4-Fluorophenylglycine is a chiral amino acid analog in which the side chain is a 4-fluorinated phenyl group attached to the glycine backbone, giving a stereogenic center at the alpha carbon (D-configuration). The molecule contains a primary amino functionality and a carboxylic acid group (or, depending on the supplied form, a corresponding protected/activated derivative), enabling standard amino acid coupling chemistry and subsequent derivatization. The para-fluorine substituent modulates aromatic electronics and can participate in specific noncovalent interactions, while also serving as a stable handle for later functional-group transformations or spectroscopic tracking. The overall structure makes D-4-Fluorophenylglycine a practical chiral building block for peptide and peptidomimetic synthesis, as well as a stereodefined intermediate for downstream medicinal chemistry and process-oriented fine chemical routes.
1. Peptide Synthesis
D-4-Fluorophenylglycine is used in peptide building-block preparation for solid-phase or solution-phase assembly where a D-configured amino acid is required for conformational control and protease resistance in peptide analogs. The amino and carboxyl functionalities support peptide coupling after conversion to an N-protected form and, when needed, activation of the carboxyl group using common coupling strategies compatible with aromatic amino acids. The 4-fluoro-substituted phenyl side chain influences aromatic packing and can tune hydrophobicity and binding-site interactions in peptide scaffolds. Incorporation of the D-amino acid into linear peptides and cyclic constraints can enable structure-focused studies of stereochemical effects and can generate downstream synthetic targets for research-grade peptidomimetics.
2. Peptidomimetics And SAR
D-4-Fluorophenylglycine serves as a chiral fragment for peptidomimetic construction in structure-activity relationship (SAR) studies where aromatic fluorination is used to probe binding determinants and electronic effects. The para-fluorine substituent provides a chemically stable substituent that can be retained through amide bond formation, ring closure, and late-stage functionalization, supporting systematic analog generation. The D-stereocenter allows stereochemically defined placement of the aromatic glycine unit to assess how inversion alters backbone geometry and receptor or enzyme recognition. The resulting fluorinated amino acid-derived motifs can be carried forward into medicinal chemistry intermediate libraries and can support iterative scaffold optimization through well-defined stereochemical inputs.
3. Chiral Intermediate Synthesis
D-4-Fluorophenylglycine is applied as a stereochemically defined chiral amino acid intermediate for manufacturing routes that require a D-configured aromatic glycine unit. The presence of both an amino group and a carboxylic acid enables conversion into protected amino acid derivatives, activated esters, or coupling-ready intermediates that can be processed under controlled, reproducible chemical steps. The fluorinated aromatic side chain can withstand many standard protecting-group manipulations, making it suitable for multi-step synthesis where side-chain integrity matters. Downstream, the compound can be used to prepare chiral intermediates for specialty chemical production, including fluorinated building blocks used in fine chemical synthesis and process chemistry intermediate streams.
4. Chemical Biology Probes
D-4-Fluorophenylglycine is suitable for chemical biology research where fluorinated aromatic residues are incorporated to enable spectroscopic monitoring, affinity tuning, or controlled labeling strategies in peptide-based probes. The aromatic fluorine can function as a stable structural marker during synthesis and analytical characterization, while the amino acid backbone supports incorporation into probe scaffolds that undergo subsequent conjugation. The D-configuration can be leveraged to modulate stability against enzymatic degradation, supporting longer-lived probe constructs in biochemical assays that rely on peptide integrity. The compound's functional-group pattern enables transformation into N-protected coupling partners and, after scaffold assembly, can support downstream derivatization toward bioconjugation-ready probe formats.
5. Analytical Standards
D-4-Fluorophenylglycine is used to prepare analytical standards and reference materials for method development in amino acid analysis, peptide hydrolysate profiling, and stereochemical verification of D-amino acid incorporation. The defined D-stereochemistry and the para-fluoro substituent facilitate chromatographic and spectroscopic differentiation from nonfluorinated or L-configured analogs. The amino acid functionality allows conversion into derivatized forms for detection workflows and can be employed as a calibration component when quantifying fluorinated amino acid residues in complex mixtures. The resulting reference-grade materials support quality control and analytical research workflows that track amino acid derivatization, peptide coupling outcomes, and stereochemical fidelity in synthetic programs.
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