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 synthetic peptide fragment featuring N-terminal tert-butyloxycarbonyl (Boc) protection, a histidine residue with trityl (Trt) side-chain protection, the noncanonical α-aminoisobutyric acid (Aib), and glutamic acid with tert-butyl (OtBu) side-chain protection, terminating in a glycine residue with a free carboxyl group. This compound exemplifies a structurally diverse peptide sequence, integrating both standard and nonstandard amino acids, and is designed for advanced research in peptide chemistry and structural biology. Its array of protecting groups makes it especially relevant for solid-phase peptide synthesis (SPPS) strategies, while its unique sequence composition supports investigations into peptide conformation, stability, and function.
Peptide synthesis optimization: The protected tetrapeptide serves as a valuable intermediate for researchers developing or refining SPPS protocols. The incorporation of orthogonal protecting groups on the side chains and N-terminus enables precise, stepwise elongation of peptide chains without undesired side reactions. Its compatibility with standard deprotection and coupling reagents allows for efficient assembly of more complex peptides, facilitating method development, troubleshooting, and validation of synthetic strategies in academic and industrial laboratories.
Conformational studies: The inclusion of α-aminoisobutyric acid (Aib) within the sequence provides a model system for investigating the influence of noncanonical residues on peptide secondary structure. Aib is known to induce helical conformations and restrict backbone flexibility, making this peptide fragment a useful tool for probing structural motifs via spectroscopic techniques such as NMR or circular dichroism. Insights gained from such studies can inform the rational design of stable peptide scaffolds for diverse research applications.
Peptide-based library construction: The modular protection pattern and accessible C-terminal carboxyl group make this compound suitable for combinatorial library synthesis. Researchers can use it as a building block in the generation of peptide libraries for screening interactions with proteins, nucleic acids, or other biomolecules. Its design supports high-throughput synthesis workflows, enabling the rapid exploration of sequence-activity relationships in drug discovery, enzymology, or biomolecular recognition studies.
Protease substrate design: The sequence and protection scheme present in this tetrapeptide allow for its use as a precursor in the synthesis of custom substrates for proteolytic enzyme assays. Upon selective deprotection and further modification, it can be tailored to generate substrates with defined cleavage sites, supporting the study of protease specificity, kinetics, and inhibition. Such applications are critical in fundamental enzymology research and in the development of biochemical tools for probing proteolytic pathways.
Analytical method development: Due to its defined sequence and multiple protecting groups, this peptide fragment is an ideal reference material for validating chromatographic and mass spectrometric techniques employed in peptide analysis. Researchers can use it to assess the performance of HPLC, LC-MS, or related analytical platforms, optimizing conditions for separation, detection, and quantification of protected and deprotected peptide species. This supports rigorous quality control and method validation in peptide research and manufacturing environments.
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