The Science Behind Fmoc-D-Phe(4-Cl)-OH: Properties, Synthesis, and Applications
Fmoc-D-Phe(4-Cl)-OH, or N-alpha-(9-Fluorenylmethyloxycarbonyl)-4-chloro-D-phenylalanine, is a sophisticated amino acid derivative that plays a crucial role in advanced organic synthesis, particularly in the field of peptide chemistry. Its structure combines the protective functionality of the Fmoc group with the unique chemical characteristics imparted by the 4-chlorophenyl moiety on a D-phenylalanine scaffold. Understanding the science behind this compound, from its synthesis to its diverse applications, is key for researchers working with peptides.
The synthesis of Fmoc-D-Phe(4-Cl)-OH typically involves the reaction of D-4-chlorophenylalanine with 9-fluorenylmethyl chloroformate (Fmoc-Cl) or a similar activating agent. This process selectively attaches the Fmoc group to the alpha-amino nitrogen, rendering it stable under typical peptide synthesis conditions but readily cleavable by mild bases like piperidine. The resulting product is usually obtained as a white crystalline powder, with purity levels critical for successful peptide synthesis. Manufacturers like NINGBO INNO PHARMCHEM CO.,LTD. employ rigorous quality control measures to ensure high enantiomeric purity and chemical integrity, which are vital for preventing epimerization and side reactions during peptide chain elongation.
The primary application of Fmoc-D-Phe(4-Cl)-OH lies in solid-phase peptide synthesis (SPPS). Its inclusion in the synthesis of peptides can modulate their biological activity, enhance their resistance to proteases, or improve their pharmacokinetic profiles. For instance, the 4-chloro substitution can influence binding affinities to specific receptors or enzymes, making it a valuable tool for developing targeted therapies. Researchers looking to buy Fmoc-D-Phe(4-Cl)-OH often seek it for its proven utility in creating complex peptidomimetics, custom peptides for research, and peptide-based drug candidates.
Beyond SPPS, Fmoc-D-Phe(4-Cl)-OH finds application in areas such as chemical biology, where it can be used to synthesize labeled peptides for imaging or diagnostic purposes. Its ability to be incorporated into peptide sequences allows for the exploration of structure-activity relationships and the development of novel biomaterials. NINGBO INNO PHARMCHEM CO.,LTD. provides this essential chemical, supporting scientific endeavors that require precision and reliability in synthetic chemistry, thereby enabling advancements in drug discovery and fundamental biological research.
Perspectives & Insights
Data Seeker X
“The synthesis of Fmoc-D-Phe(4-Cl)-OH typically involves the reaction of D-4-chlorophenylalanine with 9-fluorenylmethyl chloroformate (Fmoc-Cl) or a similar activating agent.”
Chem Reader AI
“This process selectively attaches the Fmoc group to the alpha-amino nitrogen, rendering it stable under typical peptide synthesis conditions but readily cleavable by mild bases like piperidine.”
Agile Vision 2025
“The resulting product is usually obtained as a white crystalline powder, with purity levels critical for successful peptide synthesis.”