Fmoc-L-His(Trt)-OH
- Createtime: 2024-09-04
- Updatetime: 2024-09-04
Product Details
CAS |
109425-51-6
|
PU |
99%
|
MF |
C40H33N3O4
|
EINECS |
439-640-4
|
Chemical Name: Fmoc-L-His(Trt)-OH
Molecular Formula: C37H31N3O4
Molecular Weight: 581.67 g/mol
Overview
Fmoc-L-His(Trt)-OH is a protected amino acid derivative frequently used in solid-phase peptide synthesis (SPPS). This compound features the Fmoc (9-fluorenylmethyloxycarbonyl) group protecting the amino group of histidine, while the side chain imidazole group is protected by a Trt (triphenylmethyl, also known as trityl) group. These protecting groups are essential for ensuring selective reactions during peptide synthesis, preventing unwanted side reactions and allowing for the controlled assembly of peptide chains.
Importance in Peptide Synthesis
In peptide synthesis, the Fmoc strategy is highly valued for its efficiency and mild deprotection conditions, usually involving a base such as piperidine. Fmoc-L-His(Trt)-OH is crucial when synthesizing peptides containing histidine residues, as the Trt group safeguards the imidazole side chain, which is prone to undesired reactions due to its nucleophilicity.
Histidine is an amino acid of significant biological importance, involved in enzyme active sites, metal ion binding, and the regulation of pH in proteins. Its incorporation into synthetic peptides is vital for replicating the functionality of natural proteins and for designing novel peptides with therapeutic or research applications.
Applications
Fmoc-L-His(Trt)-OH is widely used in the synthesis of peptides with specific sequences and functionalities, including those used in drug development, enzyme studies, and biomaterial research. The protected form of histidine allows for the creation of peptides that can mimic natural proteins, facilitating the study of enzyme mechanisms, receptor interactions, and the design of peptide-based drugs.
One key application of Fmoc-L-His(Trt)-OH is in the synthesis of histidine-rich peptides, which can bind metal ions and are involved in various biological processes. These peptides are important in developing therapeutic agents, such as metal-chelating drugs, and in studying metalloproteins.
Handling and Storage
As with most chemical reagents, Fmoc-L-His(Trt)-OH should be handled with care, stored in a cool, dry place, and protected from light and moisture to prevent degradation. It is typically kept in airtight containers under refrigeration to maintain its stability and reactivity over time.
Conclusion
Fmoc-L-His(Trt)-OH is an essential reagent in peptide synthesis, enabling the precise incorporation of histidine residues into peptide chains. Its use in SPPS ensures that peptides are synthesized with high fidelity, allowing researchers to create peptides with specific biological activities and functions. This compound plays a crucial role in advancing the fields of biochemistry, drug development, and molecular biology by facilitating the synthesis of complex peptides with significant biological relevance.