Fmoc-L-Glu(OtBu)-OH
- Createtime: 2024-09-04
- Updatetime: 2024-09-04
Product Details
CAS |
71989-18-9
|
PU |
99%
|
MF |
C24H27NO6
|
EINECS |
276-253-8
|
Chemical Name: Fmoc-L-Glu(OtBu)-OH
Molecular Formula: C26H27NO6
Molecular Weight: 449.50 g/mol
Overview
Fmoc-L-Glu(OtBu)-OH is a protected amino acid derivative commonly used in solid-phase peptide synthesis (SPPS). This compound features L-glutamic acid with its amino group protected by an Fmoc (9-fluorenylmethyloxycarbonyl) group, and its side-chain carboxyl group protected by a t-butyl ester (OtBu). These protective groups are essential in preventing undesired reactions during peptide synthesis, allowing for precise incorporation of L-glutamic acid into the peptide chain.
Importance in Peptide Synthesis
The Fmoc strategy is widely favored in SPPS due to its mild deprotection conditions, typically using a base like piperidine. Fmoc-L-Glu(OtBu)-OH is crucial for synthesizing peptides containing glutamic acid residues, as the OtBu group protects the side-chain carboxyl group from premature reactions. This ensures that the carboxyl group remains intact until the desired point in the synthesis process.
Glutamic acid is an amino acid that plays a significant role in protein structure and function. It is involved in various biological processes, including neurotransmission, metabolism, and the formation of the glutamate-glutamine cycle. Its incorporation into synthetic peptides is essential for replicating the functionality of natural proteins and for designing novel peptides with therapeutic or research applications.
Applications
Fmoc-L-Glu(OtBu)-OH is extensively used in the synthesis of peptides that require the presence of glutamic acid residues. These peptides are important in drug development, enzyme studies, and the creation of biomaterials. The ability to protect and later deprotect the side-chain carboxyl group allows for the creation of peptides with specific sequences and functionalities.
For example, glutamic acid-rich peptides are important in developing proteins involved in neurotransmission, as glutamate is a major excitatory neurotransmitter in the brain. Additionally, synthetic peptides containing glutamic acid residues are used in studying protein-protein interactions and in the development of enzyme inhibitors.
Handling and Storage
Fmoc-L-Glu(OtBu)-OH should be handled with care, like all chemical reagents. It is typically stored in a cool, dry place, away from light and moisture, to prevent degradation. Proper storage conditions ensure that the compound remains stable and reactive, making it suitable for use in peptide synthesis.
Conclusion
Fmoc-L-Glu(OtBu)-OH is an essential reagent in peptide synthesis, enabling the precise incorporation of L-glutamic acid into peptide sequences. Its role in SPPS allows for the creation of peptides with specific biological activities, making it a valuable tool in advancing research and therapeutic development. The use of Fmoc-L-Glu(OtBu)-OH continues to contribute to the fields of biochemistry, molecular biology, and drug discovery, allowing scientists to design and synthesize peptides with desired properties and functions.