L-Cyclohexylalanine丨CAS 27527-05-5

L-Cyclohexylalanine (CAS 27527-05-5) is a non-proteinogenic amino acid widely used in peptide synthesis, medicinal chemistry, and biochemical research. It is incorporated into peptides and peptidomimetics to modify hydrophobicity, steric bulk, and conformational behavior, often improving binding affinity and selectivity toward biological targets. The compound is frequently applied in the design of enzyme inhibitors, receptor ligands, and peptide-based drug candidates, particularly where enhanced metabolic stability is desired. In addition, L-cyclohexylalanine is used in structure–activity relationship studies to evaluate the impact of bulky hydrophobic side chains on peptide folding, bioactivity, and resistance to enzymatic degradation. It also serves as a chiral building block in the synthesis of complex pharmaceutical intermediates.

The benefits of L-cyclohexylalanine arise from its well-defined stereochemistry, strong hydrophobic character, and structural rigidity. The cyclohexyl side chain increases steric bulk and lipophilicity, which can enhance target binding and improve peptide stability against proteolysis. Its L-configuration ensures compatibility with standard peptide synthesis methods and predictable incorporation into biologically active sequences. The compound is chemically stable, easy to handle, and compatible with common coupling reagents used in solid-phase and solution-phase peptide synthesis. These features make it an effective tool for fine-tuning peptide properties and optimizing the pharmacological profile of peptide-based compounds.