• 1. Novel methodology for the solid-phase synthesis of phosphinic peptides
  Jens Buchardt,Morten Meldal J. Chem. Soc. Perkin Trans. 1 2000 3306

Introduction to Fmoc-D-Pro-OPfp (CAS No. 125281-38-1)

Fmoc-D-Pro-OPfp, with the CAS number 125281-38-1, is a versatile reagent widely used in the field of peptide synthesis and chemical biology. This compound, formally known as 9H-fluoren-9-ylmethoxycarbonyl-D-proline 2,3,5,6-tetrafluorophenyl ester, plays a crucial role in the synthesis of peptides and other bioactive molecules. Its unique properties make it an indispensable tool in both academic research and industrial applications.

The Fmoc (9-fluorenylmethoxycarbonyl) protecting group is a key feature of this compound. It is widely used in solid-phase peptide synthesis (SPPS) due to its stability under mild conditions and its ease of removal with piperidine. The D-Pro (D-proline) moiety, on the other hand, is an important amino acid derivative that can introduce stereochemical diversity into peptides, making it valuable for the synthesis of enantiomerically pure compounds.

The OPfp (2,3,5,6-tetrafluorophenyl ester) group is another critical component of Fmoc-D-Pro-OPfp. This group enhances the reactivity of the carboxylic acid during coupling reactions, facilitating efficient and selective formation of amide bonds. The combination of these functional groups makes Fmoc-D-Pro-OPfp a powerful reagent for the synthesis of complex peptides and peptidomimetics.

Recent advancements in chemical biology have further highlighted the importance of Fmoc-D-Pro-OPfp. For instance, a study published in the Journal of Medicinal Chemistry demonstrated the use of this reagent in the synthesis of novel peptidomimetic inhibitors targeting protein-protein interactions (PPIs). These inhibitors have shown promise in modulating signaling pathways involved in various diseases, including cancer and neurodegenerative disorders.

In another notable application, researchers at the University of California used Fmoc-D-Pro-OPfp to synthesize cyclic peptides with enhanced stability and bioavailability. These cyclic peptides were found to be effective in penetrating cell membranes and delivering therapeutic payloads to target cells. This work has significant implications for the development of new drug delivery systems and targeted therapies.

The versatility of Fmoc-D-Pro-OPfp extends beyond peptide synthesis. It has also been utilized in the development of combinatorial libraries for high-throughput screening. By incorporating this reagent into library synthesis protocols, researchers can rapidly generate large numbers of structurally diverse compounds for drug discovery and lead optimization.

In addition to its synthetic applications, Fmoc-D-Pro-OPfp has been employed in analytical chemistry for the derivatization of amino acids and peptides. The formation of fluorescent derivatives using this reagent allows for sensitive detection and quantification by techniques such as high-performance liquid chromatography (HPLC) and mass spectrometry (MS). This has proven invaluable in proteomics studies and clinical diagnostics.

The safety profile of Fmoc-D-Pro-OPfp is another important consideration. While it is a potent reagent, proper handling and storage practices can minimize potential hazards. It is recommended to use appropriate personal protective equipment (PPE) such as gloves, goggles, and lab coats when working with this compound. Additionally, it should be stored in a cool, dry place away from incompatible materials.

In conclusion, Fmoc-D-Pro-OPfp (CAS No. 125281-38-1) is a highly versatile reagent with a wide range of applications in peptide synthesis, chemical biology, drug discovery, and analytical chemistry. Its unique combination of functional groups makes it an essential tool for researchers aiming to develop novel bioactive molecules and therapeutic agents. As research continues to advance, the importance of this compound is likely to grow, driving further innovations in the field.

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