H-Lys(Z)-OBzl·HCl, with the CAS number 6366-70-7, is a doubly protected L-lysine derivative, also known as Nα-Benzyloxycarbonyl-L-lysine benzyl ester hydrochloride. Its molecular formula is C₂₄H₂₉ClN₂O₄, and its molecular weight is 445.0 g/mol. It features two orthogonal protecting groups: Z (benzyloxycarbonyl) protecting the α-amino group and OBzl (benzyl ester) protecting the carboxyl group, retaining the L-configuration of lysine. This unique protection strategy ensures selective reactivity, making it an indispensable building block in peptide synthesis, pharmaceutical research, and organic synthesis.
Physically, it appears as a white to off-white crystalline powder or granular solid. It has a melting point of approximately 178-182℃ and is soluble in polar organic solvents such as methanol, ethanol, and dimethylformamide, while slightly soluble in water and insoluble in non-polar solvents. It is optically active, with a specific rotation [α]²⁰/D of +12.0° to +16.0° (in methanol, c=1). It has low hygroscopicity and remains stable under normal temperature and pressure when stored properly, facilitating easy handling, storage, and formulation in solid-phase and solution-phase peptide synthesis processes.
Chemically, the orthogonal protecting groups are its core feature. The Z group is cleavable under catalytic hydrogenation or mild acidic conditions, while the OBzl group is also cleavable under catalytic hydrogenation, enabling stepwise deprotection during peptide chain assembly. This ensures the integrity of the peptide backbone and avoids unwanted side reactions. The hydrochloride salt form enhances its solubility in polar solvents and improves its stability, making it compatible with standard peptide synthesis protocols.
Its core application is in peptide synthesis, serving as a key intermediate for constructing lysine-containing peptides. It is widely used in the synthesis of therapeutic peptides, peptide hormones, enzyme inhibitors, and protein fragments. The dual protection ensures high purity and structural integrity of the final peptide product, reducing side reactions such as racemization and cross-linking.
Additionally, it is used in pharmaceutical research as a precursor for synthesizing lysine-derived drugs and in organic synthesis for preparing chiral compounds. Safety-wise, it is generally recognized as safe 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 prevent decomposition. With its excellent protection performance and biocompatibility, it is a vital raw material in peptide chemistry and pharmaceutical development.
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