Boc-p-fluoro-DL-Phe-OH

Boc-p-fluoro-DL-Phe-OH is a protected phenylalanine derivative featuring a Boc-protected amino group and a p-fluoro-substituted aromatic side chain, supplied as a DL mixture. This structure makes it a practical amino acid building block for assembling fluorinated peptide segments while maintaining the protected backbone required for controlled coupling chemistry. The presence of the para-fluorine substituent is frequently leveraged in peptide and peptidomimetic design to tune physicochemical properties and support fluorine-enabled structural characterization in downstream workflows.

1. Fluorinated Peptide Synthesis

Boc-p-fluoro-DL-Phe-OH is used as an amino acid building block for incorporating a para-fluorinated phenylalanine residue into peptide synthesis campaigns, including custom peptide manufacturing and academic peptide chemistry. The Boc protection on the amino functionality supports stepwise assembly strategies where the amino group must remain masked during activation and coupling of the growing peptide chain. Researchers commonly select this derivative when they need a fluorinated aromatic side chain for structure-activity relationship (SAR) studies or for generating peptides that are compatible with fluorine-sensitive analytical readouts.

2. Peptidomimetic And SAR Building

Boc-p-fluoro-DL-Phe-OH serves as a convenient starting building block for medicinal chemistry programs developing peptidomimetics and fluorinated analog series. The para-fluoro substitution on the phenyl ring provides a chemically stable handle that can be retained through multi-step intermediate synthesis to support comparative studies across analogs. In practice, medicinal chemistry groups use this protected amino acid derivative to generate fluorinated fragments that can be stitched into larger scaffolds, enabling systematic evaluation of how aromatic fluorination impacts properties relevant to chemical biology tool development and lead optimization.

3. Pharmaceutical Intermediate Development

Boc-p-fluoro-DL-Phe-OH is also applied as a protected fluorinated amino acid intermediate for downstream synthesis of specialty intermediates used in research-scale and industrial chemical development. Because the amino group is protected and the aromatic ring bears a defined para-fluoro substituent, the material fits workflows where fluorinated aromatic amino acid motifs must be carried through to later functionalization steps. Process chemists and intermediate developers often choose this derivative when they need a robust, isolable precursor that can be converted into fluorinated building blocks for further coupling, derivatization, or incorporation into larger drug-discovery-relevant structures.

4. Fluorine-Enabled Analytical Standards

Boc-p-fluoro-DL-Phe-OH is leveraged in analytical method development and reference material preparation for fluorine-containing peptide and amino acid studies. The para-fluoro aromatic motif supports workflows that monitor fluorinated species using fluorine-aware detection approaches and helps ensure that reference compounds contain the same fluorinated substructure as the target analytes. Analytical chemistry teams use this protected building block to prepare fluorinated internal standards or calibration components for LC-MS/MS method scouting and for verifying identity in fluorinated peptide series.

1. Store-operated Ca2+ entry sustains the fertilization Ca2+ signal in pig eggs

2. Urinary Metabolites Associated with Blood Pressure on a Low-or High-Sodium Die

3. Identification, Localization in the Central Nervous System and Novel Myostimulatory Effect of Allatostatins in Tenebrio molitor Beetle

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

5. Uncarboxylated osteocalcin decreases insulin-stimulated glucose uptake without affecting insulin signaling and regulators of mitochondrial biogenesis in myotubes