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Specifications
|
Appearance: |
White crystalline powder |
|
Assay (HPLC): |
99.0% min |
|
Single impurity (max): |
0.5% max |
|
CBZ-D-Ala: |
0.05% max |
|
Specific rotation [α]D20: |
-14° ~ -15° |
|
Melting point: |
82 ~ 86°C |
|
TLC: |
One point |
|
Moisture: |
0.5% max |
N-Carbobenzyloxy-L-alanine丨CAS 1142-20-7 is an N-protected amino acid derivative, specifically L-alanine protected at the amino group with a benzyloxycarbonyl (Cbz or Z) group. This protecting group is commonly used in peptide synthesis to prevent side reactions at the amino terminus. It plays a central role in solid-phase and solution-phase peptide chemistry.
Applications
1. Peptide Synthesis
Used extensively as a protected building block in solid-phase peptide synthesis (SPPS) and solution-phase synthesis.
The Cbz group protects the amino functionality during coupling reactions, preventing unwanted side reactions.
After chain assembly, the Cbz group can be removed by hydrogenolysis (H₂/Pd) to expose the free amine.
2. Pharmaceutical and Biochemical Research
Utilized in the synthesis of bioactive peptides, peptidomimetics, and pharmaceutical intermediates.
Useful in the design of enzyme substrates and inhibitors, especially for protease-related studies.
3. Enzyme Substrate Studies
Serves as a substrate or intermediate in enzymatic resolution and studies involving proteolytic enzymes (e.g., trypsin, chymotrypsin).
4. Chiral Intermediate
Acts as a chiral building block in the synthesis of optically active compounds.
Used in asymmetric synthesis where stereocontrol is essential.
Benefits
Cbz protection is stable under mild basic and acidic conditions, allowing selective reactions.
Easily removed by catalytic hydrogenation (Pd/C), making it ideal for orthogonal protection schemes.
Maintains the chirality and chemical integrity of L-alanine during synthesis.
Compatible with a wide range of peptide coupling reagents.
Summary
N-Carbobenzyloxy-L-alanine丨CAS 1142-20-7 is a widely used protected amino acid in organic synthesis, particularly in peptide chemistry. Its stable and removable Cbz group makes it an essential reagent for controlled peptide assembly, offering both synthetic flexibility and chemical stability. It is a crucial intermediate in pharmaceuticals, biochemical studies, and chiral molecule design.
