Mastering Peptide Synthesis: The Role of H-Asp(OBzl)-OBzl HCl
In the sophisticated world of peptide synthesis, precision and control are paramount. At Ningbo Inno Pharmchem Co., Ltd., we understand the critical role that each building block plays in creating high-quality peptide products. Among these essential components is H-Asp(OBzl)-OBzl HCl (CAS 6327-59-9), a protected derivative of L-aspartic acid that offers significant advantages in both solution-phase and solid-phase peptide synthesis (SPPS). Understanding its properties and applications is key to unlocking advanced peptide design and drug discovery.
L-Aspartic acid dibenzyl ester hydrochloride is characterized by the protection of its two carboxyl groups as benzyl esters, with the alpha-amino group present as a hydrochloride salt. This dual protection strategy is foundational to successful peptide synthesis. The benzyl ester groups are robust enough to withstand the conditions of typical coupling reactions, including those involving other protecting groups like Boc (tert-butyloxycarbonyl) and Fmoc (9-fluorenylmethoxycarbonyl).
The strategic advantage of H-Asp(OBzl)-OBzl HCl lies in its orthogonality. This means that the benzyl protecting groups can be removed selectively, often through catalytic hydrogenation (e.g., using Pd/C and hydrogen gas) or strong acid treatment, without affecting other protecting groups on the peptide chain. This allows chemists to precisely control the deprotection and subsequent reaction steps, essential for building complex peptide sequences. For instance, in the synthesis of peptidomimetics or constrained peptide analogues, where structural integrity and specific modifications are crucial, the controlled deprotection of the aspartic acid side chain is vital.
Ningbo Inno Pharmchem Co., Ltd. leverages compounds like H-Asp(OBzl)-OBzl HCl to support innovative research and development. Its application extends beyond simple peptide chain elongation to the creation of novel bioconjugates. Once the benzyl groups are removed, the free carboxyl groups on the aspartic acid residue can serve as attachment points for drugs, imaging agents, or other functional molecules, paving the way for targeted therapies and advanced diagnostic tools.
Furthermore, the compound is instrumental in the synthesis of non-ribosomal peptide analogue (NRPS) molecules. These complex natural products often feature non-proteinogenic amino acids, and their synthetic counterparts require sophisticated protection and coupling strategies, where H-Asp(OBzl)-OBzl HCl plays a significant role. Our commitment at Ningbo Inno Pharmchem Co., Ltd. is to provide researchers with the high-purity reagents necessary to push the boundaries of chemical biology and pharmaceutical innovation.
Perspectives & Insights
Agile Reader One
“The benzyl ester groups are robust enough to withstand the conditions of typical coupling reactions, including those involving other protecting groups like Boc (tert-butyloxycarbonyl) and Fmoc (9-fluorenylmethoxycarbonyl).”
Logic Vision Labs
“This means that the benzyl protecting groups can be removed selectively, often through catalytic hydrogenation (e.”
Molecule Origin 88
“, using Pd/C and hydrogen gas) or strong acid treatment, without affecting other protecting groups on the peptide chain.”