Ne-Boc-L-lysine丨CAS 2418-95-3

Ne-Boc-L-lysine丨CAS 2418-95-3, is a protected form of the natural amino acid L-lysine, in which the ε-amino group (side chain) is protected with a tert-butyloxycarbonyl (Boc) group. This modification is crucial in peptide synthesis and protein engineering, enabling selective reactions and preventing unwanted side-chain interactions during multi-step synthesis processes.

1. Solid-Phase Peptide Synthesis (SPPS)
● Ne-Boc-L-lysine丨CAS 2418-95-3 is widely used in Fmoc-based peptide synthesis to prevent unwanted side-chain reactions.
● The Boc group on the ε-amino prevents it from reacting during peptide chain elongation.
● Once synthesis is complete, the Boc group is selectively removed using mild acid (e.g., TFA), allowing for post-synthetic modification or cross-linking.
2. Site-Specific Modifications of Peptides and Proteins
● Incorporating Ne-Boc-L-lysine allows researchers to:
o Protect the ε-amino group during synthesis
o Modify it selectively after deprotection
● Used to introduce chemical handles (e.g., fluorophores, biotin, drugs) at precise lysine positions.
3. Chemical Biology and Bioorthogonal Chemistry
● Essential in unnatural amino acid mutagenesis or protein labeling strategies.
● Allows for selective attachment of functional groups (e.g., click chemistry tags) after Boc removal.
4. Polymer and Materials Science
● Used as a monomer or functional unit in the design of peptide-based hydrogels, biodegradable polymers, or self-assembling nanostructures.
● Protects reactive groups during polymerization steps.
5. Medicinal Chemistry and Drug Design
● Incorporated into peptidomimetics and cyclic peptides to increase stability, specificity, or cell permeability.
● Helps in the design of prodrugs and targeted delivery systems by masking reactive lysine residues.

1. Orthogonal Protection Strategy
● The Boc group is stable under basic conditions but removable under mild acidic conditions, offering selective deprotection without affecting other protective groups like Fmoc.
● This allows precise functionalization of lysine side chains in complex peptide synthesis.
2. Prevents Side Reactions
● In unprotected lysine, the ε-amino group can cause branching or undesired cross-linking during peptide coupling.
● Boc protection ensures linear and high-fidelity peptide chains.
3. High Purity and Reproducibility
● Commercially available with high purity, ensuring consistency in research and industrial synthesis.
● Compatible with automated peptide synthesizers and widely adopted in GLP/GMP peptide manufacturing.
4. Versatility in Functional Group Introduction
● Once deprotected, the ε-amine can be modified with a wide range of molecules, making it useful in designing:
o Fluorescent probes
o Affinity tags
o Covalent inhibitors
o Imaging agents

Ne-Boc-L-lysine丨CAS 2418-95-3 is a key building block in peptide and protein chemistry, enabling controlled protection of the lysine side chain during synthesis. Its orthogonal protection, chemical stability, and functional versatility make it indispensable in solid-phase peptide synthesis, bioengineering, chemical biology, and materials science. Whether used to prevent side reactions or to enable post-synthetic modifications, Ne-Boc-L-lysine provides precise control and chemical flexibility for complex molecular design.