N6-Cbz-L-Lysine, with the CAS number 1155-64-2, is a protected derivative of the essential amino acid L-lysine, also known as Nε-Carbobenzoxy-L-lysine or Z-L-Lys-OH. Its molecular formula is C₁₄H₂₀N₂O₄, and its molecular weight is 280.32 g/mol. It features a Cbz (carbobenzoxy) protecting group attached to the ε-amino group of L-lysine, retaining the L-configuration and inherent physiological activity while enhancing chemical stability, making it widely applied in peptide synthesis, pharmaceutical research, and biochemistry fields.
Physically, N6-Cbz-L-Lysine appears as a white to off-white crystalline powder or granular solid. It has a melting point of approximately 205-210℃ (decomposition) and is slightly soluble in cold water, more soluble in hot water, and readily soluble in common organic solvents such as methanol, ethanol, and dimethylformamide. It is optically active, with a specific rotation [α]²⁰/D of +14.0° to +18.0° (in water, c=2). It has low hygroscopicity and remains stable under normal temperature and pressure when stored properly, facilitating easy handling, storage, and formulation.
Chemically, the Cbz protecting group on the ε-amino group is the key feature that distinguishes it from free L-lysine, preventing unwanted side reactions during peptide synthesis while allowing selective deprotection under mild conditions (e.g., catalytic hydrogenation). It retains the α-amino group and carboxyl group of L-lysine, enabling it to participate in peptide bond formation. It is stable under neutral and weakly acidic conditions but may undergo deprotection or decomposition under strong acid, strong alkali, or high-temperature environments.
Its core applications focus on peptide synthesis and pharmaceutical research. As a protected amino acid building block, it is widely used in solid-phase and solution-phase peptide synthesis, enabling the controlled assembly of peptide chains by protecting the ε-amino group of lysine. It is particularly valuable in synthesizing complex peptides, including therapeutic peptides, where precise control of amino group reactivity is critical.
In the pharmaceutical industry, it serves as a key intermediate for synthesizing peptide drugs, antiviral agents, and protein-based therapeutics. In biochemistry research, it is used as a biochemical reagent for studying amino acid metabolism, enzyme activity, and peptide structure-function relationships. Safety-wise, it is generally recognized as safe (GRAS) under normal handling, with mild irritation potential upon direct contact. It should be stored in a sealed, cool, dry, and dark environment at 2-8℃, away from oxidants, moisture, and high temperatures to maintain stability and purity. With its excellent protectiveness and biocompatibility, it is an indispensable raw material in peptide chemistry and pharmaceutical development.
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