Boc-his(trt)-aib-glu(otbu)-gly-OH is a protected peptide fragment featuring sterically constrained Aib and stabilized side-chain protections. Researchers employ it to study helix stabilization, hydrogen-bond patterns, and controlled deprotection strategies. The motif supports mechanistic peptide synthesis. Its orthogonal protections allow selective transformations.
CAT No: R2499
CAS No:1890228-73-5
Synonyms/Alias:1890228-73-5;((S)-5-(tert-Butoxy)-2-(2-((S)-2-((tert-butoxycarbonyl)amino)-3-(1-trityl-1H-imidazol-4-yl)propanamido)-2-methylpropanamido)-5-oxopentanoyl)glycine;BOC-HIS(TRT)-AIB-GLU(OTBU)-GLY-OH;MFCD34597380;DB-384809;E79905;[(2S)-5-(tert-butoxy)-2-{2-[(2S)-2-[(tert-butoxycarbonyl)amino]-3-[1-(triphenylmethyl)imidazol-4-yl]propanamido]-2-methylpropanamido}-5-oxopentanamido]acetic acid;
Boc-his(trt)-aib-glu(otbu)-gly-OH is a synthetically designed tetrapeptide featuring a combination of protected amino acid residues, including N-Boc-histidine (trityl), alpha-aminoisobutyric acid (Aib), glutamic acid (O-t-butyl), and glycine. This compound is characterized by its sequence-specific architecture and orthogonally protected side chains, which make it a valuable intermediate in peptide synthesis workflows. Its unique structure supports advanced research in peptide modification, conformational studies, and the development of peptide-based biomaterials. The presence of both hydrophobic and hydrophilic residues, as well as sterically demanding protecting groups, allows researchers to explore novel folding patterns and interactions, facilitating the design of structurally diverse peptide analogs.
Peptide Synthesis: Boc-his(trt)-aib-glu(otbu)-gly-OH serves as a versatile building block in solid-phase peptide synthesis (SPPS), enabling the sequential assembly of longer peptide chains with precise control over sequence and protecting group strategy. The orthogonal protection of histidine, glutamic acid, and the N-terminus ensures compatibility with a wide range of coupling reagents and deprotection conditions, allowing for selective functionalization or extension at specific sites. As a result, this tetrapeptide is frequently utilized in the synthesis of custom peptides, peptide libraries, and modified analogs for structure-activity relationship studies.
Structure-Activity Relationship (SAR) Studies: Researchers employ this peptide fragment in SAR investigations to probe the effects of sequence variations and side-chain modifications on biological activity. By incorporating Boc-his(trt)-aib-glu(otbu)-gly-OH into peptide analogs, scientists can systematically analyze how changes in residue composition and protecting group patterns influence receptor binding, enzymatic stability, or conformational preferences. This approach is essential for optimizing peptide leads in drug discovery and for understanding the molecular basis of peptide-protein interactions.
Conformational Analysis: The inclusion of alpha-aminoisobutyric acid (Aib) in the sequence imparts notable conformational rigidity, making this tetrapeptide a valuable model for studying secondary structure formation, such as helices or turns. Spectroscopic and computational analyses of this compound enable researchers to investigate the impact of backbone constraints and side-chain protection on peptide folding and stability. Insights gained from these studies inform the rational design of foldamers, helix-stabilized peptides, and other structurally constrained biomolecules.
Peptidomimetic Design: The unique sequence and protection scheme of Boc-his(trt)-aib-glu(otbu)-gly-OH support its use in the development of peptidomimetics—molecules that mimic the structure and function of natural peptides while exhibiting enhanced stability or bioavailability. By serving as a scaffold for the introduction of non-natural residues, cyclic constraints, or functional groups, this tetrapeptide aids in the creation of novel analogs with improved pharmacological properties or resistance to proteolytic degradation. Such innovations are highly valuable in the search for next-generation therapeutics and molecular probes.
Biomaterials Research: The protected tetrapeptide is also employed in the design and synthesis of peptide-based biomaterials, such as hydrogels, nanofibers, or surface coatings. Its modular architecture and orthogonal protection facilitate site-specific conjugation, cross-linking, or functionalization, enabling the tailored fabrication of materials with desired mechanical, chemical, or biological properties. These biomaterials find application in tissue engineering, drug delivery, and biosensing, where controlled peptide assembly and presentation are critical for performance.
Boc-his(trt)-aib-glu(otbu)-gly-OH thus offers an essential toolkit for researchers engaged in advanced peptide synthesis, structural biology, and biomaterials engineering. Its sequence-specific design, strategic protection, and conformational attributes make it a preferred choice for constructing complex peptide architectures, probing structure-function relationships, and developing innovative materials for life sciences research. By leveraging its versatility, scientists can accelerate the discovery and optimization of functional peptides, peptidomimetics, and peptide-based materials, contributing to progress across multiple domains of chemical and biological investigation.
2. Autoinhibition and phosphorylation-induced activation of phospholipase C-γ isozymes
5. TMEM16F and dynamins control expansive plasma membrane reservoirs
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