Fmoc-Ser(tBu)-Gly-OH
- Createtime: 2024-09-05
- Updatetime: 2024-09-05
Product Details
CAS |
81672-17-5
|
MF |
C24H28N2O6
|
Fmoc-Ser(tBu)-Gly-OH is a dipeptide utilized in peptide synthesis, characterized by the presence of the Fmoc (9-fluorenylmethyloxycarbonyl) protective group and the amino acids serine (Ser) and glycine (Gly). This compound is valuable in peptide chemistry due to its role in introducing specific functional groups and controlling peptide structure and stability.
Structure and Components:
Fmoc Group: The Fmoc group is a widely used protective group for the N-terminus in peptide synthesis. It prevents undesired reactions during the peptide assembly process. The Fmoc group can be removed with mild base treatments, such as piperidine, facilitating the sequential addition of amino acids in solid-phase peptide synthesis (SPPS).
Serine (Ser): Serine is a polar amino acid with a hydroxyl group in its side chain, which makes it important for interactions such as hydrogen bonding. In Fmoc-Ser(tBu)-Gly-OH, the hydroxyl group of serine is protected by a tert-butyl (tBu) group to prevent unwanted reactions during synthesis. This protection is essential for controlling the reactivity of the serine residue until the desired stage of peptide assembly.
Glycine (Gly): Glycine is the simplest amino acid with a single hydrogen atom as its side chain. Its small size and flexibility make it ideal for introducing conformational freedom and facilitating tight turns or specific structural features within peptides.
Applications:
Peptide Synthesis: Fmoc-Ser(tBu)-Gly-OH is employed in peptide synthesis where a combination of a protected serine and a flexible glycine residue is required. The Fmoc protection strategy allows for precise assembly of peptides with controlled sequences and properties.
Functional Studies: The serine residue, with its hydroxyl group, can participate in various biological interactions, such as hydrogen bonding or enzyme activity. The tBu protection of serine’s hydroxyl group allows for its controlled use in functional studies and in peptides with specific activities.
Pharmaceutical Development: Peptides incorporating Fmoc-Ser(tBu)-Gly-OH may be used in drug design to achieve specific biological functions or interactions. The ability to protect and later deprotect the serine residue allows for the design of peptides with tailored properties for therapeutic applications.
Biotechnology: In biotechnology, this dipeptide can be utilized to create peptide-based materials or biosensors. The combination of a protected serine and a flexible glycine can be adapted for designing materials with specific functional characteristics, including molecular recognition and detection.
Conclusion:
Fmoc-Ser(tBu)-Gly-OH is a crucial dipeptide in peptide chemistry, offering a blend of functional and flexible properties. Its use in solid-phase peptide synthesis, functional studies, and pharmaceutical development highlights its importance in creating peptides with specific characteristics. By incorporating Fmoc-Ser(tBu)-Gly-OH, researchers and developers can design peptides with precise structural and functional attributes, advancing various scientific and industrial applications.