• 1. Endo-β-N-Acetylglucosaminidase catalysed glycosylation: tolerance of enzymes to structural variation of the glycosyl amino acid acceptor
  Yusuke Tomabechi,Marie A. Squire,Antony J. Fairbanks Org. Biomol. Chem. 2014 12 942
• 2. Synthesis of thiourea-tethered C-glycosyl amino acids viaisothiocyanate–amine coupling
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• 3. An asparagine/tryptophan organogel showing a selective response towards fluoride anions
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• 4. A novel organogelator incorporating tert-butyl esters of asparagines
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• Solvents and Organic Chemicals Organic Compounds Organic acids and derivatives Carboxylic acids and derivatives Amino acids, peptides, and analogues Amino acids and derivatives
• Solvents and Organic Chemicals Organic Compounds Acids/Esters

Comprehensive Guide to L-Asparagine tert-butyl ester (CAS No. 25456-86-4): Properties, Applications, and Industry Insights

L-Asparagine tert-butyl ester (CAS No. 25456-86-4) is a protected derivative of the naturally occurring amino acid L-asparagine, widely utilized in peptide synthesis and pharmaceutical research. This compound features a tert-butyl ester group, which enhances its stability and solubility in organic solvents, making it a valuable building block for drug discovery and biochemical studies. With the growing demand for peptide-based therapeutics, L-Asparagine tert-butyl ester hydrochloride and related derivatives have gained significant attention in the biotech and pharmaceutical industries.

The molecular structure of L-Asparagine tert-butyl ester includes a chiral center, ensuring its role in stereospecific reactions. Researchers often employ this compound in solid-phase peptide synthesis (SPPS) due to its compatibility with Fmoc and Boc protection strategies. Recent trends highlight its use in developing anticancer peptides and neuroprotective agents, aligning with the surge in interest around targeted therapies and personalized medicine. Common search queries like "L-Asparagine tert-butyl ester synthesis" or "CAS 25456-86-4 applications" reflect its relevance in academic and industrial settings.

From a technical perspective, 25456-86-4 exhibits a white crystalline powder morphology under standard conditions, with a molecular weight of 202.23 g/mol. Its stability in anhydrous environments makes it suitable for long-term storage, though precautions against moisture are recommended. Analytical techniques such as HPLC and NMR are routinely used to verify its purity, a critical factor given its applications in GMP-grade pharmaceutical production. Discussions on platforms like ResearchGate often focus on optimizing its coupling efficiency in peptide chains, addressing common challenges like racemization.

Environmental and safety profiles of L-Asparagine tert-butyl ester are frequently queried, particularly in light of green chemistry initiatives. While not classified as hazardous, proper lab handling protocols—including PPE and ventilation—are advised. The compound’s biodegradability and low ecotoxicity align with the industry’s shift toward sustainable intermediates, a topic dominating conferences like the American Peptide Symposium. Innovations in enzymatic synthesis routes further enhance its appeal for eco-conscious manufacturers.

Market analysts project steady growth for amino acid derivatives like 25456-86-4, driven by expanding peptide drug pipelines. Key players are investing in scalable production methods to meet demand from clinical-stage biotechs. For researchers exploring its potential, databases like PubChem and Reaxys provide curated data on its physicochemical properties and synthetic pathways. As peptide therapeutics enter mainstream medicine, L-Asparagine tert-butyl ester remains a cornerstone of modern medicinal chemistry.

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