Boc-DL-Arg-OH HCl H2O
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Boc-DL-Arg-OH HCl H2O

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Category
BOC-Amino Acids
Catalog number
BAT-000799
Molecular Formula
C11H22N4O4·HCl·H2O
Molecular Weight
328.8
Synonyms
N-Boc-DL-arginine hydrochloride monohydrate
Storage
Store at 2-8 °C

Boc-DL-Arg-OH HCl H2O, a protected form of the amino acid arginine, plays a pivotal role in biochemical and pharmaceutical research. Here are the key applications presented with a high degree of perplexity and burstiness:

Peptide Synthesis: Integral to peptide synthesis, Boc-DL-Arg-OH HCl H2O serves as a shielded arginine residue, preserving the reactivity of the arginine side chain during peptide chain elongation. This compound is essential for constructing peptides with utmost purity and precision, critical for the production of synthetic peptides utilized in both research and therapeutic realms. Its significance lies in facilitating the assembly of peptides with intricate sequences and specific structural demands.

Enzyme Studies: Delving into enzyme studies, this compound aids in elucidating the role of arginine residues in the structure and function of enzymes. By employing protected forms like Boc-DL-Arg-OH HCl H2O, researchers can manipulate enzymes to explore their catalytic activity and interaction with substrates. This endeavor contributes to unraveling enzyme mechanisms and designing enzyme inhibitors for therapeutic applications.

Pharmaceutical Development: In the realm of pharmaceutical development, Boc-DL-Arg-OH HCl H2O plays a vital role in the creation of arginine-containing pharmaceutical compounds. Post-synthesis, the Boc protection group is removed, yielding pristine arginine derivatives suitable for incorporation into drugs. This strategy is indispensable for crafting novel therapeutics with enhanced efficacy and diminished side effects.

Protein Engineering: Within the domain of protein engineering, Boc-DL-Arg-OH HCl H2O is utilized to introduce arginine residues at precise locations within proteins. This modification elevates protein stability, solubility, and interaction with other molecules, pivotal for tailoring proteins with desired functions. Such engineered proteins find applications in diagnostics, therapeutics, and industrial biotechnology, heralding a new era of customizable protein design.

1. Mode specificity in the HCl + OH → Cl + H2O reaction: Polanyi's rules vs sudden vector projection model
Hongwei Song, Hua Guo J Phys Chem A. 2015 Feb 5;119(5):826-31. doi: 10.1021/jp512021m. Epub 2015 Jan 22.
The dynamics and mode specificity of the HCl + OH → Cl + H2O reaction are investigated using a full-dimensional quantum dynamics method on an accurate global potential energy surface. It is shown that the vibrational excitation of the HCl reactant greatly enhances the reactivity while the OH vibrational excitation has little effect. The surprising HCl vibrational enhancement of this early barrier reaction contradicts a naive extension of Polanyi's rules, but can be explained by the sudden vector projection model, which attributes the promotional effect of the HCl vibration to its strong coupling with the reaction coordinate at the transition state. In addition, it is found that the fundamental and overtone excitations of the HCl reactant change the reaction mechanism from a direct barrier crossing process to a capture-like process.
2. Superconcentrated hydrochloric acid
Kun Huang, et al. J Phys Chem B. 2011 Jun 23;115(24):7823-9. doi: 10.1021/jp109551z. Epub 2011 May 26.
We report the discovery of a potentially useful superconcentrated HCl at ambient temperature and pressure by using a simple surfactant-based reversed micelle system. Surprisingly, the molar ratios of H(+) to H(2)O (denoted as n(H+)/n(H2O)) in superconcentrated HCl can be larger than 5, while the maximum achievable n(H+)/n(H2O) value for conventional saturated HCl aqueous solution (37 wt %) is only about 0.28. Furthermore, both NMR and FT-IR results indicate that a significant amount of HCl remains in the molecular form rather than being ionized into H(+) and Cl(-). The superconcentrated HCl may promote some organic reactions that are not feasible by using conventional 37 wt % HCl solution. For example, addition reaction between C═C and HCl occurs in superconcentrated HCl solution without using catalysts.
3. The exothermic HCl + OH·(H2O) reaction: removal of the HCl + OH barrier by a single water molecule
Guoliang Li, Hui Wang, Qian-Shu Li, Yaoming Xie, Henry F Schaefer 3rd J Chem Phys. 2014 Mar 28;140(12):124316. doi: 10.1063/1.4869518.
The entrance complex, transition state, and exit complex for the title reaction have been investigated using the CCSD(T) method with correlation consistent basis sets up to cc-pVQZ. The stationary point geometries for the reaction are related to but different from those for the water monomer reaction HCl + OH → Cl + H2O. Our most important conclusion is that the hydrogen-bonded water molecule removes the classical barrier entirely. For the endothermic reverse reaction Cl + (H2O)2, the second water molecule lowers the relative energies of the entrance complex, transition state, and exit complex by about 4 kcal/mol. The title reaction is exothermic by 17.7 kcal/mol. The entrance complex HCl⋯OH·(H2O) is bound by 6.9 kcal/mol relative to the separated reactants. The classical barrier height for the reverse reaction is predicted to be 16.5 kcal/mol. The exit complex Cl⋯(H2O)2 is found to lie 6.8 kcal/mol below the separated products. The potential energy surface for the Cl + (H2O)2 reaction is radically different from that for the valence isoelectronic F + (H2O)2 system.
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