The Chemistry and Applications of Boc-Cys(Acm)-OH in Peptide Research
In the intricate field of peptide chemistry, the precise manipulation of amino acid building blocks is key to synthesizing functional peptides. Boc-Cys(Acm)-OH (CAS 19746-37-3), or N-Boc-S-acetamidomethyl-L-cysteine, is a specialty amino acid derivative that plays a critical role in this process. Its unique chemical structure, featuring the N-Boc protecting group and the S-Acm protecting group on the cysteine thiol, provides essential control for chemists engaged in peptide synthesis.
Chemically, Boc-Cys(Acm)-OH is characterized by its molecular formula C11H20N2O5S and a molecular weight of approximately 292.35 g/mol. It typically appears as a white powder, which is a common and convenient physical form for handling in laboratory settings. Its stability, often recommended to be stored at 4°C, ensures its efficacy for extended periods when proper storage conditions are maintained. This derivative is fundamental for introducing cysteine residues into peptide chains, particularly when specific disulfide bond formations or other cysteine-related modifications are planned after the peptide backbone is assembled.
The primary application of Boc-Cys(Acm)-OH is within solid-phase peptide synthesis (SPPS). During SPPS, the N-Boc group is selectively removed using acidic reagents (e.g., trifluoroacetic acid), allowing for the sequential addition of subsequent amino acids. The S-Acm group on cysteine remains intact throughout these steps, protecting the highly reactive thiol moiety. Post-synthesis, the Acm group can be efficiently cleaved using reagents like silver nitrate or iodine under mild conditions, often in the presence of oxidizing agents to promote the formation of native disulfide bonds or other desired linkages. This controlled deprotection strategy is vital for creating peptides with specific conformational properties or biological activities.
Beyond basic peptide chain assembly, Boc-Cys(Acm)-OH is also utilized in more advanced peptide modification strategies. Researchers might employ it for site-specific labeling, conjugation to other molecules, or the synthesis of peptide-based therapeutics where precise side-chain chemistry is essential. For any researcher or company looking to buy Boc-Cys(Acm)-OH, understanding its chemical behavior and synthesis utility is crucial. As a leading supplier and manufacturer in China, NINGBO INNO PHARMCHEM CO.,LTD. provides this high-quality intermediate. We offer reliable access to this chemical, understanding its importance for research and development in areas such as drug discovery and biochemistry. Inquire about our product specifications and price to ensure your peptide synthesis projects are supported by the finest chemical building blocks available.
Perspectives & Insights
Silicon Analyst 88
“The S-Acm group on cysteine remains intact throughout these steps, protecting the highly reactive thiol moiety.”
Quantum Seeker Pro
“Post-synthesis, the Acm group can be efficiently cleaved using reagents like silver nitrate or iodine under mild conditions, often in the presence of oxidizing agents to promote the formation of native disulfide bonds or other desired linkages.”
Bio Reader 7
“This controlled deprotection strategy is vital for creating peptides with specific conformational properties or biological activities.”