H-m-Fluoro-D-Phe-OMe · HCl

H-m-Fluoro-D-Phe-OMe · HCl is a D-configured fluoro-substituted phenylalanine methyl ester salt, where the chiral amino acid core bears a meta-fluorine on the aromatic ring and a methyl ester at the carboxylate position. The HCl salt form indicates the presence of a protonated amine, which improves handling of the amino ester while maintaining a functional primary amine for subsequent protection or coupling chemistry. The aromatic fluorine provides a strong handle for electronic tuning, ^19F NMR tracking, and selective derivatization through standard aryl chemistry logic, while the ester functionality supports conversion to activated carboxyl derivatives for peptide bond formation. The D stereochemistry supports stereocontrolled construction of enantiomerically defined peptide segments and chiral intermediates for medicinal chemistry and structure-based synthetic planning.

1. Peptide Synthesis

H-m-Fluoro-D-Phe-OMe · HCl supports peptide building block preparation in solid-phase or solution-phase workflows by providing a D-phenylalanine framework with a protected carboxyl equivalent as a methyl ester. The protonated amine can be converted into an N-protected amino acid derivative compatible with peptide coupling, while the meta-fluoro aromatic ring remains stable under typical peptide assembly conditions. Carboxylate activation strategies can be applied after ester transformation to generate a coupling-ready acid or activated ester, enabling incorporation of the D-configured residue into peptide chains. Downstream, the resulting fluoro-containing peptides can be used for residue-specific SAR work, stereochemical mapping, and analytical method development using the fluorine signal.

2. Peptidomimetics And SAR

H-m-Fluoro-D-Phe-OMe · HCl is suitable for peptidomimetic and SAR studies where a D-amino acid segment and an aryl fluorine together influence conformational preferences and electronic properties. The meta-fluorine can be retained through amide bond formation and can serve as a spectroscopic reporter for monitoring analog synthesis and conformational changes in solution. The amino ester format enables derivatization into protected amino acid intermediates that feed into iterative analog construction, including C-terminal modification routes after ester hydrolysis or activation. Fluoro-substituted D-phenylalanine analogs generated from this intermediate can be employed in structure-activity relationship studies and molecular scaffold diversification for non-natural peptide-like chemotypes.

3. Chemical Biology Labeling

H-m-Fluoro-D-Phe-OMe · HCl can be applied to chemical biology workflows that require stable, traceable amino acid incorporation into biomolecule-modifying reagents. The D stereocenter and fluoroaryl motif provide stereochemically defined residues that can be introduced into peptides or peptide-like linkers used for biochemical probing and target-binding studies. The ester and amine functionality support conversion into coupling partners for attaching linkers, tags, or affinity handles through standard peptide coupling or amide-forming chemistry. The presence of the aromatic fluorine enables ^19F-based detection strategies for monitoring labeling efficiency and tracking reagent distribution in analytical research contexts.

4. Chiral Building Block Development

H-m-Fluoro-D-Phe-OMe · HCl functions as a chiral amino acid intermediate for stereoselective synthesis programs that require D-configuration control at the amino acid alpha-carbon. The D-phenylalanine backbone can be carried through protection-group strategies for the amine and conversion of the methyl ester into activated carboxylic acid derivatives, supporting downstream assembly of enantiopure chiral fragments. The meta-fluoro substituent offers an additional stereochemical and electronic element that can be preserved to maintain a defined substitution pattern in final chiral products. Resulting derivatives can be used as intermediates for chiral library synthesis, enantiomer-specific SAR exploration, and process-compatible fine chemical manufacturing of fluorinated amino acid derivatives.

5. Pharmaceutical Intermediate Preparation

H-m-Fluoro-D-Phe-OMe · HCl is applicable to pharmaceutical intermediate preparation for manufacturing routes that require fluorinated, D-configured amino acid building blocks for drug-like scaffold construction. The amino ester salt form supports controlled handling prior to conversion into N-protected amino acid derivatives and carboxyl-activated intermediates used in amide bond formation. The meta-fluoro aromatic group is chemically robust and can be maintained through multi-step synthesis, enabling incorporation into peptide-like fragments, linker regions, or constrained binding motifs. Industrially relevant downstream utility includes preparation of fluoro-substituted chiral intermediates for fine chemical synthesis and process chemistry intermediate streams feeding larger molecule assembly.

6. Analytical Research Standards

H-m-Fluoro-D-Phe-OMe · HCl can serve as an analytical reference material for method development and characterization of fluorinated amino acid derivatives. The combination of a defined D stereochemistry and a meta-fluoro aromatic group provides a distinct spectroscopic signature, including ^19F NMR observables, that can be used to confirm incorporation and monitor impurity profiles in intermediate and final products. The methyl ester and protonated amine functionality support conversion into standardized derivatives used for calibration, identity testing, and comparative analysis across synthetic batches. Broader relevance extends to analytical support for peptide coupling chemistry, stereochemical verification, and quality control of fluorinated amino acid building blocks used in biochemical research workflows.

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