Boc-His(Boc)-Aib-Glu(O-tBu)-Gly-OH
[CAS# 1169630-31-2]

Identification

• Classification: Biochemical >> Common amino acids and protein drugs
• Name: Boc-His(Boc)-Aib-Glu(O-tBu)-Gly-OH
• Synonyms: 2-[[(2S)-2-[[2-methyl-2-[[(2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-3-[1-[(2-methylpropan-2-yl)oxycarbonyl]imidazol-4-yl]propanoyl]amino]propanoyl]amino]-5-[(2-methylpropan-2-yl)oxy]-5-oxopentanoyl]amino]acetic acid
• Protein Sequence: XXXG
• Molecular Formula: C₃₁H₅₀N₆O₁₁
• Molecular Weight: 682.76
• CAS Registry Number: 1169630-31-2
• SMILES: CC(C)(C)OC(=O)CC[C@@H](C(=O)NCC(=O)O)NC(=O)C(C)(C)NC(=O)[C@H](CC1=CN(C=N1)C(=O)OC(C)(C)C)NC(=O)OC(C)(C)C

Discovory and Applicatios

Boc-His(Boc)-Aib-Glu(O-tBu)-Gly-OH is a synthetic peptide widely used in peptide chemistry and related fields. The structure of this compound contains five amino acid residues, each protected with specific groups to prevent unwanted reactions during synthesis. "Boc" stands for tert-butyloxycarbonyl, which is a protecting group for the amino terminus of the peptide. "His(Boc)" refers to histidine, an amino acid with an additional Boc protecting group on its imidazole side chain. "Aib" refers to α-aminoisobutyric acid, a non-proteinogenic amino acid. "Glu(O-tBu)" denotes glutamic acid with a tert-butyl ester protecting the carboxyl group of its side chain. "Gly" is glycine, a simple amino acid. The carboxyl end of the peptide remains free (-OH), ready for further reaction or extension.

This peptide was developed as part of the growing demand for synthetic peptides used in various research and pharmaceutical applications. Peptide synthesis has been an essential technique since the mid-20th century, allowing researchers to create specific sequences of amino acids that mimic or interfere with biological processes. The Boc-His(Boc)-Aib-Glu(O-tBu)-Gly-OH peptide is used primarily in research settings, particularly in the study of protein-protein interactions, peptide-based drug development, and understanding how modifications to peptide sequences affect their stability, folding, and function.

One of the most significant applications of this peptide is in the field of drug discovery. Researchers use synthetic peptides like Boc-His(Boc)-Aib-Glu(O-tBu)-Gly-OH to investigate potential therapeutic agents for diseases that involve protein malfunction or peptide signaling, such as cancer or autoimmune disorders. The introduction of non-proteinogenic amino acids like Aib into peptide sequences can enhance the stability and bioavailability of peptides in biological environments, which is critical for developing peptide-based drugs.

Moreover, this peptide is commonly used in solid-phase peptide synthesis (SPPS), a method developed by Robert Bruce Merrifield in 1963, which revolutionized the production of peptides. In SPPS, amino acids are sequentially added to a growing peptide chain anchored to a solid resin, with each step involving the removal of protecting groups like Boc and the formation of peptide bonds. The protecting groups in Boc-His(Boc)-Aib-Glu(O-tBu)-Gly-OH ensure that the correct bonds are formed at each stage, avoiding unwanted side reactions. Once synthesized, the protecting groups are removed, yielding the desired peptide for use in various applications.

Boc-His(Boc)-Aib-Glu(O-tBu)-Gly-OH is also used in the study of peptide conformations. The presence of Aib, which induces helical structures, allows researchers to explore the structural properties of peptides in solution. This is particularly valuable in understanding how peptides fold and how their three-dimensional structures influence their biological activity.

As a chemically stable and versatile synthetic peptide, Boc-His(Boc)-Aib-Glu(O-tBu)-Gly-OH serves as an important tool in both basic research and applied sciences. Its design reflects the intricate balance of protecting groups and amino acid sequence modifications necessary to create functional and stable peptides for research and potential therapeutic use.