Overview
HCTU is a uranium-type peptide coupling reagent developed as an alternative to HBTU and HATU. It combines the reactivity of chlorobenzotriazole with tetramethyluronium salts, offering reduced racemization during amino acid activation. The hexafluorophosphate counterion enhances solubility in organic solvents while maintaining stability. Widely adopted in pharmaceutical research, HCTU is particularly valued for synthesizing complex peptides and modified amino acids. Its efficiency in solid-phase peptide synthesis (SPPS) has made it a staple in combinatorial chemistry and drug discovery workflows.
Physical and Chemical Properties
HCTU forms hygroscopic crystals that require careful moisture control. The compound exhibits excellent thermal stability up to 150°C before decomposition. Its solubility profile favors polar aprotic solvents like DMF (50-100 mg/mL), with limited solubility in water or nonpolar solvents. The reagent activates carboxyl groups within 5-15 minutes at room temperature, generating active esters with minimal epimerization. Kinetic studies show superior performance over HOBt-based reagents in sterically hindered couplings. The hexafluorophosphate anion contributes to improved crystallinity compared to tetrafluoroborate analogs.
Main Applications
In peptide synthesis, HCTU is primarily used with DIEA as a base for Fmoc- or Boc-protected amino acids. It achieves >95% coupling yields for standard sequences and maintains efficiency in difficult couplings (e.g., Aib-NMe amino acids). The pharmaceutical industry employs HCTU for producing peptide therapeutics like GLP-1 analogs and antimicrobial peptides. Its low racemization makes it ideal for synthesizing stereochemically pure compounds. Researchers also utilize HCTU in bioconjugation for labeling proteins with fluorescent probes or PEG chains.
Safety and Storage
As a reactive chemical, HCTU requires handling with nitrile gloves and safety goggles. Avoid inhalation of powder and contact with skin - wash immediately with water if exposed. The compound is moisture-sensitive and should be stored under argon or nitrogen in sealed containers. Decomposition products include toxic hydrogen fluoride gas when heated above 200°C. Always use in fume hoods with proper acid gas scrubbers. Shelf life is typically 2-3 years when stored at 2-8°C with desiccant.
B2B Procurement Guide
When sourcing HCTU, prioritize suppliers with ISO 9001 certification and analytical certificates (COA). Key specifications to verify include: ≥98% purity (HPLC), ≤0.3% water content (KF titration), and ≤0.5% residual solvents (GC). Bulk purchases (1kg+) often qualify for 15-30% discounts. Consider manufacturers offering customized packaging (e.g., 100g bottles with septum seals) for moisture-sensitive applications. For international shipments, ensure cold chain logistics with temperature monitoring.
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