Overview
Cyclohexylalanine is a synthetic non-proteinogenic amino acid featuring a cyclohexyl group attached to the alanine backbone. It is primarily used in pharmaceutical research and peptide chemistry due to its structural properties. The compound is chiral, typically supplied as the L-enantiomer for biological applications. Unlike natural amino acids, cyclohexylalanine is not incorporated into proteins but serves as a building block for modified peptides and drug candidates. Its hydrophobic cyclohexyl side chain makes it valuable for studying protein-protein interactions and designing enzyme inhibitors.
Physical and Chemical Properties
Cyclohexylalanine appears as a white crystalline solid with good stability under standard conditions. It exhibits moderate solubility in water (approximately 10-20 mg/mL) and higher solubility in polar organic solvents like methanol or DMSO. The compound's melting point with decomposition occurs around 280-290°C. The cyclohexyl group contributes significant hydrophobicity, with a calculated logP value of approximately 1.5-2.0. This property influences its behavior in chromatographic separations and biological systems. The amino acid maintains zwitterionic character in aqueous solutions at physiological pH, similar to standard amino acids.
Main Applications
In pharmaceutical development, cyclohexylalanine serves as a key intermediate for peptidomimetic drugs targeting GPCRs and proteases. Its constrained cyclohexyl side chain helps stabilize specific peptide conformations and enhance metabolic stability. The compound finds particular use in oncology and neurology research, where modified peptides require hydrophobic residues for membrane penetration or target binding. Additionally, it's employed in solid-phase peptide synthesis (SPPS) as a specialty building block for structure-activity relationship (SAR) studies.
Safety and Storage
While not classified as highly hazardous, cyclohexylalanine requires standard laboratory precautions. Use appropriate personal protective equipment including gloves and safety glasses. Avoid generating dust during handling, and work in a well-ventilated area or fume hood when weighing powdered material. For long-term storage, keep containers tightly sealed in a cool (15-25°C), dry environment away from light. Under these conditions, the compound typically remains stable for several years. Monitor for discoloration or clumping as potential signs of degradation.
B2B Procurement Guide
When sourcing cyclohexylalanine, prioritize suppliers specializing in fine chemicals for pharmaceutical applications. Key specifications include HPLC purity (typically ≥98%), chiral purity (if applicable), and absence of heavy metals. Certificates of Analysis (CoA) should accompany each batch. For GMP applications, verify the supplier's quality systems and regulatory compliance. Consider ordering custom quantities to minimize waste of this relatively expensive specialty chemical. Lead times may vary from 2-8 weeks depending on source and customization requirements.
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