H-p-Fluoro-D-Phe-OMe · HCl

H-p-Fluoro-D-Phe-OMe · HCl is a hydrochloride salt of a methyl esterified, para-fluorinated D-phenylalanine derivative, where the amino functionality is present in a salt form and the carboxyl group is masked as an O-methyl ester. The D-configuration at the stereogenic α-carbon provides defined chiral control for stereoselective peptide coupling and for generating enantiomerically characterized analogs. The para-fluorine substituent on the aromatic ring introduces a strong electronic and steric modulation that can be leveraged in SAR studies, receptor-binding investigations, and fluorinated metabolite or binding-probe design. The ester and salt-state amino group together enable downstream transformations including selective deprotection, conversion to activated carboxylic acid derivatives, and incorporation into peptide building blocks under standard amino acid chemistry conditions.

1. Peptide Synthesis

H-p-Fluoro-D-Phe-OMe · HCl supports peptide building block preparation and coupling workflows in peptide chemistry by combining a chiral D-phenylalanine core with a protected carboxyl functionality as the methyl ester. The amino group as the hydrochloride salt can be handled to facilitate formation of peptide bonds after conversion to an appropriate free amine or activated carboxylate intermediate. The para-fluoro aromatic ring can be retained through coupling steps, enabling synthesis of fluorinated peptide analogs for structure-activity relationship studies and conformational probing. The resulting D-configured fluorinated residue is suitable for generating peptide fragments, longer peptide sequences, and peptidomimetic scaffolds where stereochemistry and aromatic electronics are controlled.

2. Unnatural Amino Acid Incorporation

H-p-Fluoro-D-Phe-OMe · HCl functions as a chiral unnatural amino acid intermediate for incorporating D-amino acid stereochemistry into synthetic peptides and protein-engineering constructs. The D-α-carbon stereocenter and the para-fluoro substituent provide a defined stereoelectronic signature that can influence backbone conformation, protease resistance, and binding-site interactions in biochemical research contexts. The methyl ester enables controlled manipulation of the carboxyl terminus during derivatization, including conversion to carboxylic acid forms for subsequent coupling or functionalization strategies. Downstream use commonly includes generating D-fluorinated amino acid-containing analogs for chemical biology studies, SAR mapping, and mechanistic investigations of peptide recognition.

3. Side-Chain Functionalization

H-p-Fluoro-D-Phe-OMe · HCl is applicable to side-chain functionalization and aromatic modification strategies because the para-fluorine can participate in targeted transformations and can serve as a stable handle for electronic tuning. The fluorinated phenyl ring can be carried through ester and salt-state handling, allowing selective downstream modifications that preserve the chiral center during intermediate construction. The methyl ester provides a manipulable carboxyl equivalent for sequential synthetic steps that may include ester hydrolysis, activation, or conversion to amide-forming derivatives in peptide or small-molecule synthesis. The compound therefore serves as a practical chiral amino acid-based intermediate for generating fluorinated derivatives used in molecular design, SAR studies, and fine chemical synthesis routes.

4. SAR Studies And Molecular Design

H-p-Fluoro-D-Phe-OMe · HCl is suited for medicinal chemistry-oriented molecular design and structure-activity relationship studies where fluorinated aromatic amino acid motifs are used to modulate binding interactions. The para-fluoro group provides a distinct physicochemical signature that can affect lipophilicity, hydrogen-bonding patterns, and metabolic stability trends in fluorinated analog series. The D-phenylalanine stereochemistry supports the construction of stereochemically defined peptide mimics and constrained analogs for comparing enantiomeric or stereoisomeric effects on target recognition. The methyl ester and salt-state amino group facilitate stepwise assembly into larger scaffolds, enabling generation of characterized fluorinated intermediates for iterative SAR campaign synthesis.

5. Pharmaceutical Intermediate Preparation

H-p-Fluoro-D-Phe-OMe · HCl can be employed in pharmaceutical intermediate preparation and process chemistry for manufacturing fluorinated amino acid derivatives and peptide-related intermediates. The hydrochloride salt form stabilizes the amine during handling and can support consistent downstream conversion to coupling-ready forms in synthetic sequences. The methyl ester functionality allows controlled management of the carboxyl group during route design, including staged deprotection or conversion to activated acid derivatives for amide bond formation. The para-fluorinated aromatic ring and D-configuration enable production of stereodefined, fluorinated building blocks used in fine chemical synthesis and specialty chemical production where chiral amino acid incorporation is required.

1. Implications of ligand-receptor binding kinetics on GLP-1R signalling

2. The effect of sex on immune responses to a homocitrullinated peptide in the DR4-transgenic mouse model of Rheumatoid Arthritis

3. Autoinhibition and phosphorylation-induced activation of phospholipase C-γ isozymes

4. Adipose tissue is a key organ for the beneficial effects of GLP-2 metabolic function

5. A possible role of tachykinin-related peptide on an immune system activity of mealworm beetle, Tenebrio molitor L