2-Fluoro-DL-Phenylalanine is a fluorinated, non-natural phenylalanine analogue bearing a benzyl side chain with a fluorine substituent at the alpha position (Cα), classifying it as an amino acid derivative with an arylalkyl functionality. The molecule contains both an amino group and a carboxyl group and is provided as the DL (racemic) stereochemical form, with the side chain retaining the phenyl ring while the alpha-fluorination alters electronic and steric characteristics around the backbone. In peptide chemistry and chemical biology, this amino acid is used as a fluorinated building block for structure-activity studies, backbone-modified peptide synthesis, and analytical method development where incorporation of an alpha-fluorinated residue provides a chemically distinct handle for NMR or mass spectrometric characterization.
CAT No: CP14403
CAS No:2629-55-2
Synonyms/Alias:2-Fluoro-dl-phenylalanine;2629-55-2;2-amino-3-(2-fluorophenyl)propanoicacid;2-Fluorophenylalanine;o-Fluoro-dl-phenylalanine;dl-(2-Fluorophenyl)alanine;o-Fluorophenylalanine;dl-o-Fluorophenylalanine;3-(o-Fluorophenyl)alanine;dl-beta-o-Fluorophenylalanine;H-DL-PHE(2-F)-OH;DL-2-FLUOROPHENYLALANINE;NYCRCTMDYITATC-UHFFFAOYSA-N;ALANINE,3-(o-FLUOROPHENYL)-;ST024950;2-Amino-3-(2-fluorophenyl)propionicAcid;2-Amino-3-(2-fluoro-phenyl)-propionicacid;35175-89-4;Phenylalanine,2-fluoro-;(R)-2-FluorophenylalanineHydrochloride;DL-o-phenylalanine;325-69-9;ACMC-20a4dk;2-Fluorophenylalanine#;ACMC-1CMU9
2-Fluoro-DL-Phenylalanine is a fluorinated phenylalanine analog supplied as a DL mixture, combining the amino acid backbone with a side-chain fluorine that can influence conformational preferences and physicochemical behavior in downstream molecules. This non-proteinogenic amino acid building block is commonly used in peptide and peptidomimetic synthesis and in medicinal chemistry programs where halogen substitution is leveraged for structure-activity relationship studies. Its primary amine and carboxylic acid functionality make it a practical starting material for preparing fluorinated analogs, as well as for generating standards and intermediates that require a defined fluorinated stereochemical composition.
1. Peptide And Peptidomimetic Building
2-Fluoro-DL-Phenylalanine is used by custom peptide synthesis groups and medicinal chemistry teams to incorporate a fluorinated aromatic side chain into peptide analogs and peptidomimetics. The DL stereochemical mixture supports exploratory structure-activity relationship workflows where both enantiomeric forms are evaluated in parallel, and the fluorine substituent provides a handle for tuning lipophilicity, steric/electronic effects, and metabolic fate compared with unsubstituted phenylalanine. In practice, this building block is selected when the target scaffold requires a fluorinated phenyl ring while maintaining the amino acid backbone for standard coupling strategies used in peptide intermediate preparation.
2. Medicinal Chemistry SAR Analog Synthesis
2-Fluoro-DL-Phenylalanine is frequently employed in small-molecule and peptide-like lead optimization to generate fluorinated analogs used in SAR campaigns. Medicinal chemistry researchers use this amino acid to introduce a defined fluorine atom on an aromatic side chain, enabling systematic comparison against non-fluorinated or differently substituted phenylalanine derivatives. The availability of both enantiomers as a DL mixture is particularly useful during early-stage screening and method development, where researchers prioritize rapid access to fluorinated analogs and downstream derivatization into amide, ester, or peptide-derived fragments relevant to structure-activity mapping.
3. Fluorinated Reference Standards
2-Fluoro-DL-Phenylalanine is used as a reference material for analytical method development and characterization of fluorinated amino acid derivatives, peptide fragments, and related intermediates. Analytical chemistry laboratories incorporate this compound into workflows for LC-MS and related quantitation/identity checks when a fluorinated phenylalanine analog is required as an external standard or calibration component. The defined fluorine substitution provides a distinct mass signature and chromatographic behavior relative to non-fluorinated counterparts, supporting reliable tracking of synthetic incorporation and purification performance for fluorinated targets during research and industrial development.
4. Pharmaceutical Intermediate Development
2-Fluoro-DL-Phenylalanine serves as a practical fluorinated amino acid intermediate for preparing downstream building blocks used in pharmaceutical intermediate development and specialty chemical manufacturing. Process and development chemists rely on fluorinated aromatic amino acid cores to access a range of derivatives, including protected or functionalized intermediates that feed into peptide-like structures and halogenated fragment libraries. The presence of both an amino and a carboxylic acid functional group makes it a convenient starting point for conversion into activated forms and derivative scaffolds used in multi-step manufacturing of fluorinated research compounds.
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