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BOC-L-Lysine
  • Brand:baishixing
  • Origin:sichuanchengdu
  • Createtime: 2024-09-05
  • Updatetime: 2024-09-05
Product Details
CAS 13734-28-6
MF C11H22N2O4
EINECS 237-303-4
BOC-L-Lysine is a protected form of the amino acid L-lysine, commonly used in organic synthesis, particularly in the field of peptide chemistry. The compound features an L-lysine residue with a BOC (tert-butyloxycarbonyl) group protecting its α-amino group, making it a useful intermediate in synthetic processes.

Structure and Components:
L-Lysine: Lysine is an essential amino acid and plays a critical role in protein synthesis, cell signaling, and molecular interactions due to its positively charged ε-amino group. In its natural form, lysine has two reactive amino groups: the α-amino group at the beginning of the molecule and the ε-amino group on its side chain.

BOC (tert-butyloxycarbonyl) Group: The BOC group is a widely used protective group in organic chemistry. It temporarily blocks the α-amino group of lysine to prevent it from reacting during certain steps of synthesis. This protection is necessary for selective reactions, particularly in solid-phase peptide synthesis (SPPS). The BOC group can be easily removed by treating the molecule with mild acidic conditions such as trifluoroacetic acid (TFA).

Application in Peptide Synthesis:
BOC-L-Lysine is commonly used in the stepwise synthesis of peptides. The BOC group ensures that only the desired amino groups participate in reactions, preventing unwanted side reactions. In peptide synthesis, BOC-L-Lysine is often employed in the creation of complex peptide chains where precise control over the order of amino acid coupling is crucial.

During peptide synthesis, the BOC group provides protection for the α-amino group while leaving the ε-amino group available for coupling, allowing researchers to build peptide chains in a controlled manner. Once the peptide chain is assembled, the BOC group is removed under acidic conditions, exposing the α-amino group for subsequent reactions or modifications.

Advantages:
Selective Protection: The BOC group ensures that only specific amino groups are reactive, allowing for precise control in multi-step synthetic processes.
Ease of Removal: The BOC group can be efficiently removed under mild acidic conditions without disrupting the integrity of the peptide chain.
Stability: BOC-L-Lysine provides stability during synthesis, reducing the risk of side reactions that could interfere with the peptide-building process.
Conclusion:
BOC-L-Lysine is a fundamental reagent in peptide chemistry, offering controlled protection of the α-amino group to ensure the efficient synthesis of complex peptide sequences. Its selective protection and ease of deprotection make it an indispensable tool for researchers working in peptide synthesis and other areas of biochemistry.
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