The Chemical Properties and Synthesis of Boc-Ala-OSu for Research
Boc-Ala-OSu, or N-Boc-L-alanine N-hydroxysuccinimide ester (CAS: 3392-05-0), is a crucial intermediate in the field of organic chemistry, particularly within peptide synthesis. This article explores its essential chemical properties, common synthesis routes, and its significance in driving research forward.
Chemically, Boc-Ala-OSu combines the protected alanine moiety with an activated succinimide ester. The tert-butoxycarbonyl (Boc) group is a widely used protecting group for amines in organic synthesis. It offers stability under various reaction conditions but can be readily removed using mild acidic treatments, such as trifluoroacetic acid (TFA). The N-hydroxysuccinimide (OSu) ester is an excellent leaving group, making the carbonyl carbon of the alanine residue highly susceptible to nucleophilic attack. This activation is key to its utility in forming amide bonds, the fundamental linkage in peptides.
The synthesis of Boc-Ala-OSu typically involves the coupling of Boc-L-alanine with N-hydroxysuccinimide (NHS) in the presence of a coupling agent. Common coupling agents include dicyclohexylcarbodiimide (DCC) or 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (EDC), often with additives like N-hydroxysuccinimide itself or hydroxybenzotriazole (HOBt) to suppress racemization and improve yields. The reaction is usually carried out in anhydrous organic solvents like dichloromethane (DCM), dimethylformamide (DMF), or tetrahydrofuran (THF). After the reaction, the product is typically isolated through filtration to remove by-products (like dicyclohexylurea if DCC is used) and then purified by recrystallization or chromatography. Access to such high-quality peptide synthesis reagents is vital for reliable research outcomes.
The appearance of Boc-Ala-OSu as a white to off-white solid is a common characteristic. Its molecular weight is approximately 286.28 g/mol. Its solubility in common organic solvents facilitates its incorporation into reaction mixtures. Researchers looking to buy Boc-Ala-OSu often seek materials with proven purity and reliable performance in subsequent coupling reactions.
The importance of Boc-Ala-OSu extends to various research areas. In pharmaceutical research, it is instrumental in synthesizing peptide-based drugs, which are gaining increasing attention for their therapeutic potential. Its use in custom peptide synthesis allows for the creation of specific peptide sequences for studying protein-protein interactions, developing diagnostic tools, or exploring new biomaterials. For those involved in academic research or industrial development, understanding the synthesis and properties of such key intermediates is crucial for efficient project execution.
In summary, Boc-Ala-OSu is a critical reagent in modern organic and peptide synthesis. Its well-defined chemical properties and relatively straightforward synthesis routes make it an accessible yet powerful tool for researchers. Ensuring a consistent supply of high-purity Boc-Ala-OSu from trusted sources is paramount for advancing scientific discovery and innovation.
Chemically, Boc-Ala-OSu combines the protected alanine moiety with an activated succinimide ester. The tert-butoxycarbonyl (Boc) group is a widely used protecting group for amines in organic synthesis. It offers stability under various reaction conditions but can be readily removed using mild acidic treatments, such as trifluoroacetic acid (TFA). The N-hydroxysuccinimide (OSu) ester is an excellent leaving group, making the carbonyl carbon of the alanine residue highly susceptible to nucleophilic attack. This activation is key to its utility in forming amide bonds, the fundamental linkage in peptides.
The synthesis of Boc-Ala-OSu typically involves the coupling of Boc-L-alanine with N-hydroxysuccinimide (NHS) in the presence of a coupling agent. Common coupling agents include dicyclohexylcarbodiimide (DCC) or 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (EDC), often with additives like N-hydroxysuccinimide itself or hydroxybenzotriazole (HOBt) to suppress racemization and improve yields. The reaction is usually carried out in anhydrous organic solvents like dichloromethane (DCM), dimethylformamide (DMF), or tetrahydrofuran (THF). After the reaction, the product is typically isolated through filtration to remove by-products (like dicyclohexylurea if DCC is used) and then purified by recrystallization or chromatography. Access to such high-quality peptide synthesis reagents is vital for reliable research outcomes.
The appearance of Boc-Ala-OSu as a white to off-white solid is a common characteristic. Its molecular weight is approximately 286.28 g/mol. Its solubility in common organic solvents facilitates its incorporation into reaction mixtures. Researchers looking to buy Boc-Ala-OSu often seek materials with proven purity and reliable performance in subsequent coupling reactions.
The importance of Boc-Ala-OSu extends to various research areas. In pharmaceutical research, it is instrumental in synthesizing peptide-based drugs, which are gaining increasing attention for their therapeutic potential. Its use in custom peptide synthesis allows for the creation of specific peptide sequences for studying protein-protein interactions, developing diagnostic tools, or exploring new biomaterials. For those involved in academic research or industrial development, understanding the synthesis and properties of such key intermediates is crucial for efficient project execution.
In summary, Boc-Ala-OSu is a critical reagent in modern organic and peptide synthesis. Its well-defined chemical properties and relatively straightforward synthesis routes make it an accessible yet powerful tool for researchers. Ensuring a consistent supply of high-purity Boc-Ala-OSu from trusted sources is paramount for advancing scientific discovery and innovation.
Perspectives & Insights
Logic Thinker AI
“In summary, Boc-Ala-OSu is a critical reagent in modern organic and peptide synthesis.”
Molecule Spark 2025
“Its well-defined chemical properties and relatively straightforward synthesis routes make it an accessible yet powerful tool for researchers.”
Alpha Pioneer 01
“Ensuring a consistent supply of high-purity Boc-Ala-OSu from trusted sources is paramount for advancing scientific discovery and innovation.”