Boc-his(trt)-aib-glu(otbu)-gly-OH
[CAS# 1890228-73-5]

Identification

• Classification: Biochemical >> Peptide
• Name: Boc-his(trt)-aib-glu(otbu)-gly-OH
• Synonyms: 2-[[(2S)-2-[[2-methyl-2-[[(2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-3-(1-tritylimidazol-4-yl)propanoyl]amino]propanoyl]amino]-5-[(2-methylpropan-2-yl)oxy]-5-oxopentanoyl]amino]acetic acid
• Molecular Formula: C₄₅H₅₆N₆O₉
• Molecular Weight: 824.96
• Protein Sequence: XXXG
• CAS Registry Number: 1890228-73-5
• 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(C2=CC=CC=C2)(C3=CC=CC=C3)C4=CC=CC=C4)NC(=O)OC(C)(C)C

Properties

• Density: 1.2±0.1 g/cm³, Calc.^*
• Index of Refraction: 1.583, Calc.^*
• Boiling Point: 1033.0±65.0 °C (760 mmHg), Calc.^*
• Flash Point: 578.5±34.3 °C, Calc.^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H302-H315-H319
• Safety Statements: P501-P270-P264-P280-P302+P352-P337+P313-P305+P351+P338-P362+P364-P332+P313-P301+P312+P330

Discovery and Applications

The chemical substance Boc-his(trt)-aib-glu(otbu)-gly-OH represents a synthetic peptide designed for applications in biochemical research and pharmaceutical development. This compound features a series of amino acids protected by specific chemical groups to ensure stability during synthetic processes. The systematic arrangement of amino acids, including Boc (tert-butyloxycarbonyl)-protected histidine with a trityl group, Aib (alpha-aminoisobutyric acid), glutamic acid with an OtBu (tert-butyl ester) protecting group, and glycine, provides unique properties suitable for diverse applications.

The discovery of synthetic peptides like Boc-his(trt)-aib-glu(otbu)-gly-OH stems from advancements in solid-phase peptide synthesis (SPPS). Developed in the mid-20th century, SPPS enabled the stepwise construction of peptides with high precision. This compound, in particular, demonstrates the integration of protective groups to prevent unwanted side reactions during synthesis, ensuring high yield and purity. Protective groups like Boc and trityl are easily removed under controlled conditions, allowing for subsequent functionalization or biological evaluation.

The synthesis of Boc-his(trt)-aib-glu(otbu)-gly-OH typically involves SPPS methodologies. Key steps include coupling amino acids sequentially on a resin support, employing activating agents to promote peptide bond formation. The Boc and OtBu groups provide temporary protection to the amine and carboxyl functionalities, respectively, ensuring that reactions proceed selectively. After chain assembly, the peptide is cleaved from the resin and deprotected to yield the final product. Advances in coupling reagents and purification techniques have further optimized the synthesis process.

The primary application of Boc-his(trt)-aib-glu(otbu)-gly-OH lies in its role as a model compound for studying peptide structure, folding, and interactions. The inclusion of Aib introduces structural rigidity, facilitating investigations into helical conformations and secondary structure stability. Additionally, the protected glutamic acid residue offers opportunities for site-specific modifications, such as conjugation with fluorescent probes or therapeutic agents. This peptide is also valuable in drug discovery, where it serves as a precursor for developing bioactive compounds targeting various diseases.

References

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