FMOC-Arg(Pbf)-OH
- Price: ¥1600/Kg
- Createtime: 2024-09-09
- Updatetime: 2024-09-09
Product Details
CAS |
154445-77-9
|
PU |
99%
|
MF |
C34H40N4O7S
|
FMOC-Arg(Pbf)-OH is a derivative of the amino acid arginine used primarily in peptide synthesis. The compound features an FMOC (9-fluorenylmethoxycarbonyl) protecting group on the amino group of arginine and a Pbf (2,2,4,6,7-pentamethyldihydrobenzofuran-5-sulfonyl) protecting group on the guanidine side chain of arginine. This combination of protective groups allows chemists to selectively deprotect certain functional groups during peptide synthesis, ensuring efficient and precise formation of peptide bonds.
Structure and Composition
FMOC-Arg(Pbf)-OH consists of:
FMOC Group: A widely used protecting group for amino acids in solid-phase peptide synthesis (SPPS). It is easily removed under mild basic conditions, allowing for the controlled buildup of peptide chains.
Arginine Residue: Arginine is an essential amino acid with a guanidinium group in its side chain, which gives it a positive charge under physiological conditions. This makes arginine important in interactions with nucleic acids and proteins.
Pbf Group: The Pbf group is a protecting group specifically used to shield the highly reactive guanidine group in arginine during peptide synthesis. It is stable under basic conditions but easily removed using strong acids like trifluoroacetic acid (TFA) after the synthesis is complete.
Importance in Peptide Synthesis
FMOC-Arg(Pbf)-OH is crucial for solid-phase peptide synthesis (SPPS), a method widely used in laboratory settings for producing peptides, proteins, and bioactive molecules. In SPPS, amino acids are added one by one to a growing peptide chain. The protecting groups ensure that only the intended peptide bonds form, preventing unwanted side reactions.
FMOC Protecting Group: The FMOC group shields the amino group of arginine during peptide elongation. This group is removed under mild basic conditions (e.g., piperidine), exposing the amino group for the next coupling step.
Pbf Protecting Group: The Pbf group specifically protects arginine’s side chain, preventing unwanted reactions involving the guanidinium group. The Pbf group remains intact throughout the peptide synthesis and is removed at the end with acidic conditions, preserving the integrity of the peptide chain.
Applications in Research and Industry
FMOC-Arg(Pbf)-OH plays a vital role in the synthesis of various bioactive peptides, including:
Therapeutic Peptides: Many drugs are developed using peptides due to their high specificity and activity in the body. FMOC-Arg(Pbf)-OH allows precise synthesis of peptides used in treatments for cancer, diabetes, and autoimmune disorders.
Protein Engineering: Peptides are used to design and study proteins with specific functions. The selective deprotection of FMOC-Arg(Pbf)-OH ensures the accurate formation of complex peptide structures used in protein engineering.
Biomolecular Studies: Synthetic peptides are valuable tools in studying protein-protein interactions, enzyme functions, and molecular recognition processes in biology and biochemistry.
Conclusion
FMOC-Arg(Pbf)-OH is a critical reagent in solid-phase peptide synthesis, enabling precise and controlled assembly of peptide chains. The use of FMOC and Pbf protecting groups ensures that the arginine residue’s functional groups remain intact during synthesis, allowing for the production of complex peptides and proteins. As peptide-based therapeutics and biomolecular research continue to expand, FMOC-Arg(Pbf)-OH remains a key player in advancing these fields.