The Chemistry Behind Boc-Leu-OSu: Properties and Synthesis for Peptide Bond Formation
At NINGBO INNO PHARMCHEM CO.,LTD., we are committed to providing a deep understanding of the chemical compounds we supply. Boc-L-Leucine O-Succinimidyl Ester (Boc-Leu-OSu), CAS 3392-09-4, is a key reagent whose chemistry is fundamental to effective peptide synthesis.
The molecular formula of Boc-Leu-OSu is C15H24N2O6, with a molecular weight of 328.36 g/mol. Its physical form is typically a white to off-white powder, with a melting point range of 110-113 °C. A crucial aspect of its utility is its optical activity, with a reported specific rotation ([α]20/D) of -43.5±1° (c = 1% in dioxane). This chirality is essential for building peptides with the correct three-dimensional structure.
The synthesis of Boc-Leu-OSu generally involves activating Boc-L-Leucine. A common method utilizes N,N'-Disuccinimidyl carbonate (DSC) or similar coupling reagents in the presence of a base, such as triethylamine, in an inert solvent like dichloromethane. The reaction mechanism involves the formation of an activated ester intermediate, which then reacts with N-hydroxysuccinimide to yield Boc-Leu-OSu. This process ensures the incorporation of the succinimidyl ester group, which is a good leaving group, thereby enhancing reactivity in subsequent coupling reactions.
The core function of Boc-Leu-OSu in peptide synthesis is the formation of the peptide bond. When reacted with the free amine terminus of another amino acid or peptide chain, the succinimidyl ester readily undergoes nucleophilic acyl substitution. This results in the formation of a stable amide (peptide) bond and the release of N-hydroxysuccinimide. This reaction mechanism is highly efficient, making Boc-Leu-OSu a preferred reagent for many peptide synthesis reagents applications. For those considering Boc-L-Leucine N-hydroxysuccinimide ester uses, understanding this mechanism is key to optimizing reaction conditions.
NINGBO INNO PHARMCHEM CO.,LTD. ensures that our Boc-Leu-OSu is synthesized and purified to the highest standards, providing researchers and manufacturers with a reliable tool for their synthetic needs. By understanding the chemistry behind this compound, users can better leverage its capabilities in their custom peptide synthesis solutions and other biochemical research.
Perspectives & Insights
Logic Thinker AI
“A common method utilizes N,N'-Disuccinimidyl carbonate (DSC) or similar coupling reagents in the presence of a base, such as triethylamine, in an inert solvent like dichloromethane.”
Molecule Spark 2025
“The reaction mechanism involves the formation of an activated ester intermediate, which then reacts with N-hydroxysuccinimide to yield Boc-Leu-OSu.”
Alpha Pioneer 01
“This process ensures the incorporation of the succinimidyl ester group, which is a good leaving group, thereby enhancing reactivity in subsequent coupling reactions.”