Overview
Boc-D-alanine is a chemically protected derivative of D-alanine, where the amino group is shielded by a tert-butoxycarbonyl (Boc) group. This modification enhances stability during peptide synthesis, making it a critical reagent in pharmaceutical and biochemical research. Its chiral nature ensures precise stereochemical control in synthetic pathways, particularly for producing enantiomerically pure compounds. The Boc group can be selectively removed under mild acidic conditions, allowing further functionalization without disrupting the peptide backbone.
Physical and Chemical Properties
Boc-D-alanine appears as a white crystalline powder with a molecular weight of 189.21 g/mol. It exhibits moderate solubility in polar organic solvents like dimethylformamide (DMF) and dimethyl sulfoxide (DMSO), but limited solubility in water. The compound’s melting point ranges between 85-90 °C, and its Boc protection group provides stability against nucleophilic attacks. Its infrared (IR) spectrum typically shows characteristic peaks for carbonyl (C=O) and amine (N-H) stretches, aiding in quality verification.
Main Applications
Boc-D-alanine is primarily used in solid-phase peptide synthesis (SPPS) to incorporate D-alanine residues into peptide chains while preventing unwanted side reactions. It serves as a building block for antibiotics, enzyme inhibitors, and other bioactive molecules. In pharmaceuticals, it aids in developing drugs with improved metabolic stability. Researchers also utilize it to study enzyme mechanisms or design peptidomimetics, leveraging its chiral purity to explore structure-activity relationships.
Safety and Storage
Handle Boc-D-alanine with gloves and eye protection to avoid skin or eye irritation. Ensure adequate ventilation to prevent inhalation of dust. In case of exposure, rinse affected areas with water and seek medical advice if symptoms persist. Store the compound in a tightly sealed container at 2-8 °C, away from moisture and light. Prolonged exposure to high temperatures or humidity may degrade the Boc group, reducing efficacy.
B2B Procurement Guide
When sourcing Boc-D-alanine, prioritize suppliers with certified analytical reports (e.g., HPLC, NMR) confirming purity ≥98%. Verify CAS number (7764-95-6) to avoid counterfeit products. Bulk purchases (e.g., 100g+) may reduce costs, but assess storage capabilities to prevent degradation. Request samples for pilot testing, especially for sensitive applications like GMP-compliant synthesis. Compare lead times and logistics options, as some suppliers specialize in expedited shipments for research emergencies.
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