Boc-Tyr(tBu)-Aib-OH
- Createtime: 2024-09-05
- Updatetime: 2024-09-05
Product Details
Boc-Tyr(tBu)-Aib-OH is a tripeptide derivative used in solid-phase peptide synthesis (SPPS) and other peptide synthesis techniques. It consists of two amino acids, tyrosine (Tyr) and α-aminoisobutyric acid (Aib), each with specific protective groups to facilitate controlled peptide assembly.
Structure and Components:
Boc Group (tert-butyloxycarbonyl): The Boc group is attached to the α-amino group of tyrosine, protecting it from reacting during peptide synthesis. Boc is commonly used in peptide chemistry because it is stable under mild conditions but can be easily removed using strong acids like trifluoroacetic acid (TFA).
Tyrosine (Tyr): Tyrosine is an aromatic amino acid with a hydroxyl (-OH) group attached to its phenyl side chain. It is often involved in signaling and catalytic processes in biological systems. In this compound, the hydroxyl group of tyrosine is protected by the tBu (tert-butyl) group, preventing side reactions during synthesis.
Aib (α-Aminoisobutyric Acid): Aib is a non-proteinogenic amino acid known for its ability to induce helical structures in peptides. Its rigid, branched structure provides conformational stability to peptides, making it important for designing peptides with specific structural properties.
C-terminal Carboxyl Group (-OH): The molecule has a free carboxyl group at the C-terminus, allowing for further peptide bond formation in synthesis.
Application in Peptide Synthesis:
Boc-Tyr(tBu)-Aib-OH is used as a building block in the synthesis of peptides, especially those where structural rigidity and stability are desired. The Boc group protects the α-amino group of tyrosine, while the tBu group shields the hydroxyl group on tyrosine’s side chain. These protective groups prevent unwanted side reactions, ensuring that only the targeted bonds are formed during the synthesis process.
The Aib residue plays a critical role in promoting specific structural conformations, particularly helical structures, which are important in many bioactive peptides. This makes Boc-Tyr(tBu)-Aib-OH valuable in designing peptides with defined secondary structures.
Advantages:
Selective Protection: The Boc and tBu groups protect functional groups, allowing for precise control over the peptide synthesis process.
Ease of Deprotection: The Boc group can be easily removed under acidic conditions, and the tBu group can be deprotected without affecting the peptide backbone.
Structural Stability: The Aib residue promotes α-helical conformations, adding stability and rigidity to the peptide structure, which is beneficial in developing peptides with specific biological functions.
Conclusion:
Boc-Tyr(tBu)-Aib-OH is a useful dipeptide derivative in peptide synthesis, particularly for constructing peptides with enhanced stability and specific conformational properties. The selective protection of reactive groups and the incorporation of Aib make it an essential tool for researchers developing structured and bioactive peptides in the fields of biochemistry and pharmaceuticals.