The Chemistry Behind Phosphopeptides: An Insight into Fmoc-O-benzyl-L-phosphoserine
The field of peptide chemistry is continuously expanding, with a growing emphasis on post-translational modifications that dictate protein function and signaling. Phosphorylation, the addition of a phosphate group to serine, threonine, or tyrosine residues, is one of the most common and crucial modifications. The synthesis of phosphopeptides, essential for studying these processes, relies on specialized building blocks. NINGBO INNO PHARMCHEM CO.,LTD. is dedicated to providing these critical components, such as Fmoc-O-benzyl-L-phosphoserine (CAS 158171-14-3).
Fmoc-O-benzyl-L-phosphoserine is a chemically engineered amino acid derivative designed to facilitate the incorporation of a phosphorylated serine residue into peptide chains using the Fmoc (9-fluorenylmethoxycarbonyl) solid-phase peptide synthesis (SPPS) strategy. The Fmoc group serves as a temporary amine-protecting group, which can be selectively removed under mild basic conditions (typically using piperidine). This orthogonal protection strategy is key to successful SPPS, allowing for controlled chain elongation.
The structure of Fmoc-O-benzyl-L-phosphoserine features a benzyl ether protecting group attached to the phosphate moiety. This benzyl protection is generally stable to the piperidine used for Fmoc removal, ensuring that the phosphate group remains intact during the initial stages of peptide synthesis. Once the peptide chain is assembled, the benzyl group can be removed under more vigorous conditions, such as treatment with strong acids (e.g., TFA), to reveal the free phosphoserine residue. The ability to strategically remove protecting groups at different stages is fundamental to complex organic synthesis, including advanced peptide synthesis.
The use of this specialized building block is central to research in medicinal chemistry and biochemistry. By synthesizing phosphopeptides with accuracy, scientists can investigate enzyme kinetics (kinases and phosphatases), study protein-protein interactions mediated by phosphorylation, and develop diagnostic tools. The efficiency of this process is enhanced by the compatibility of Fmoc-O-benzyl-L-phosphoserine with standard coupling reagents used in Fmoc SPPS. Researchers at NINGBO INNO PHARMCHEM CO.,LTD. understand that the purity and consistent quality of such building blocks are paramount for reproducible results.
The chemistry behind Fmoc-O-benzyl-L-phosphoserine enables the creation of sophisticated tools for biological research. Its reliable performance in synthetic protocols makes it an indispensable reagent for laboratories engaged in understanding cellular signaling, developing novel therapeutics, and advancing the field of chemical biology. NINGBO INNO PHARMCHEM CO.,LTD. is committed to supplying these high-quality chemical intermediates, empowering scientists to explore the intricate world of phosphopeptides and their biological roles.
Perspectives & Insights
Core Pioneer 24
“The ability to strategically remove protecting groups at different stages is fundamental to complex organic synthesis, including advanced peptide synthesis.”
Silicon Explorer X
“The use of this specialized building block is central to research in medicinal chemistry and biochemistry.”
Quantum Catalyst AI
“By synthesizing phosphopeptides with accuracy, scientists can investigate enzyme kinetics (kinases and phosphatases), study protein-protein interactions mediated by phosphorylation, and develop diagnostic tools.”