• 1. Stereochemical and mechanistic studies on the formation of the 3-oxoindolizidine skeleton from ornithine derivatives
  M José Domínguez,M Teresa García-López,Rosario Herranz,Mercedes Martín-Martínez,Rosario González-Mu?iz J. Chem. Soc. Perkin Trans. 1 1995 2839

• Solvents and Organic Chemicals Organic Compounds Benzenoids Benzene and substituted derivatives Benzyloxycarbonyls
• Solvents and Organic Chemicals Organic Compounds Acids/Esters

Comprehensive Guide to Boc-D-Orn(Z)-OH (CAS No. 16937-92-1): Properties, Applications, and Industry Insights

Boc-D-Orn(Z)-OH (CAS No. 16937-92-1) is a specialized N-protected amino acid derivative widely used in peptide synthesis and pharmaceutical research. This compound features a Boc (tert-butoxycarbonyl) group and a Z (benzyloxycarbonyl) moiety, offering dual protection for the D-ornithine backbone. Its unique structure makes it invaluable for constructing complex peptides with high stereochemical purity, particularly in drug discovery and bioconjugation applications.

In recent years, the demand for Boc-D-Orn(Z)-OH has surged due to its role in developing peptide-based therapeutics, a rapidly growing segment in the pharmaceutical industry. Researchers frequently search for "Boc-D-Orn(Z)-OH solubility," "Boc-D-Orn(Z)-OH synthesis protocol," or "CAS 16937-92-1 suppliers," reflecting its practical importance. The compound’s stability under acidic conditions (thanks to the Boc group) and selective deprotection capabilities (via the Z group) align with modern trends favoring modular peptide assembly.

From a technical perspective, Boc-D-Orn(Z)-OH exhibits a molecular weight of 352.38 g/mol and typically appears as a white crystalline powder. Its compatibility with solid-phase peptide synthesis (SPPS) and Fmoc/tBu strategies makes it a staple in laboratories focusing on GPCR-targeting peptides or antimicrobial peptide design. Notably, its D-configuration enhances resistance to enzymatic degradation, a critical feature for peptide drug stability—a hot topic in biopharmaceutical forums.

Quality control of CAS 16937-92-1 often involves HPLC (>98% purity) and chiral analysis to ensure enantiomeric purity. Storage recommendations (typically at 2–8°C under inert gas) are frequently searched, as improper handling may affect the Boc group’s integrity. The compound’s applications extend to linker chemistry in antibody-drug conjugates (ADCs), where its Z-protected side chain enables controlled payload release—a trending area in oncology research.

Environmental and regulatory aspects of Boc-D-Orn(Z)-OH also draw attention. While not classified as hazardous, proper waste disposal protocols are emphasized in alignment with green chemistry principles. Suppliers increasingly highlight REACH compliance and GMP-grade availability to meet pharmaceutical industry standards. This focus on sustainability resonates with current searches like "eco-friendly peptide reagents" or "Boc-D-Orn(Z)-OH lifecycle assessment."

Innovative uses of 16937-92-1 continue to emerge, such as in peptide hydrogel design for tissue engineering or as a building block for peptidomimetics. Its orthogonal protection scheme allows sequential deprotection—a feature exploited in multicomponent peptide ligation strategies. These applications position Boc-D-Orn(Z)-OH as a key player in advancing precision medicine and biomaterials science.

For researchers troubleshooting synthesis, common queries include "Boc-D-Orn(Z)-OH coupling efficiency" and "racemization risk during Z-deprotection." Best practices recommend using HOBt/DIC activation and monitoring by LC-MS. The compound’s MSDS data (highlighting non-toxicity but recommending standard lab precautions) is another frequently accessed resource, underscoring its safe yet specialized handling profile.

Market analysts note steady growth in the Boc-D-Orn(Z)-OH segment, driven by expanding peptide API manufacturing and academic research funding. Custom modifications (e.g., isotope-labeled versions for proteomics studies) are gaining traction. As peptide therapeutics address unmet needs in diabetes, obesity, and rare diseases, CAS 16937-92-1 remains a critical enabler of innovation at the chemistry-biology interface.

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