Cbz-L-tert-Leucine dicyclohexylamine salt
[CAS# 62965-37-1]

Identification

• Classification: Biochemical >> Amino acids and their derivatives >> Leucine derivative
• Name: Cbz-L-tert-Leucine dicyclohexylamine salt
• Synonyms: 3-Methyl-N-[(phenylmethoxy)carbonyl]-L-valine compd. with N-cyclohexylcyclohexanamine
• Molecular Formula: C₁₄H₁₉NO₄.C₁₂H₂₃N
• Molecular Weight: 446.63
• Protein Sequence: X
• CAS Registry Number: 62965-37-1
• EC Number: 613-119-3
• SMILES: CC(C)(C)[C@@H](C(=O)O)NC(=O)OCC1=CC=CC=C1.C1CCC(CC1)NC2CCCCC2

Properties

• Melting point: 164-167 °C
• alpha: 20

Safety Data

• Hazard Symbols: GHS07;GHS08 Danger
• Risk Statements: H302-H372-H412-H413
• Safety Statements: P260-P264-P270-P273-P301+P317-P319-P330-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Acute toxicity	Acute Tox.	4	H302
Chronic hazardous to the aquatic environment	Aquatic Chronic	3	H412
Specific target organ toxicity - repeated exposure	STOT RE	1	H372
Chronic hazardous to the aquatic environment	Aquatic Chronic	4	H413

Discovery and Applications

Cbz-L-tert-Leucine dicyclohexylamine salt is an organic compound used primarily in peptide chemistry and pharmaceutical research. With the molecular formula C25H39NO4, it features a Cbz (carbobenzyloxy) protecting group attached to L-tert-leucine, a derivative of the amino acid leucine, paired with dicyclohexylamine as the counterion. This structure plays a crucial role in protecting the amino acid during peptide synthesis and ensuring the stability and purity of peptides.

The discovery of Cbz-L-tert-Leucine dicyclohexylamine salt is rooted in the development of protecting groups for amino acids, a key aspect of peptide chemistry. Protecting groups are essential in peptide synthesis as they prevent undesired reactions at functional groups, allowing for selective modifications. The Cbz group, introduced by the chemist Karl R. O. L. C. G. Emil Fischer, is a widely used protecting group due to its stability and ease of removal. The addition of the dicyclohexylamine salt further enhances the stability of the compound by neutralizing the carboxyl group of the amino acid.

In peptide synthesis, Cbz-L-tert-Leucine dicyclohexylamine salt serves as a protected form of L-tert-leucine, allowing chemists to build peptides with high precision. The tert-butyl group on the leucine residue provides steric protection, reducing unwanted side reactions. During synthesis, the Cbz group protects the amino group, preventing it from participating in reactions until the desired steps are complete. After peptide synthesis, the Cbz group can be removed selectively to yield the final peptide with the desired sequence and functionality.

One of the primary applications of Cbz-L-tert-Leucine dicyclohexylamine salt is in the pharmaceutical industry, where it is used to produce peptide-based drugs. Peptides are essential in drug development because they can mimic biological processes or act as therapeutic agents. By using protected amino acids like Cbz-L-tert-Leucine, chemists can efficiently synthesize peptides that are used in a range of therapeutic areas, including hormones, antibiotics, and cancer treatments.

In addition to its role in pharmaceuticals, this compound is also valuable in the field of materials science. Peptides and peptide-based polymers are increasingly used to create functional materials with applications in drug delivery, tissue engineering, and biomaterials. The controlled synthesis of peptides facilitated by Cbz-L-tert-Leucine dicyclohexylamine salt enables the development of advanced materials with specific properties and functions.

Furthermore, Cbz-L-tert-Leucine dicyclohexylamine salt is used in research and development settings to study peptide synthesis and modification techniques. Researchers investigate new methods for improving the efficiency and selectivity of peptide synthesis, exploring how variations in protecting groups and counterions affect the overall process.

In summary, Cbz-L-tert-Leucine dicyclohexylamine salt is a significant compound in peptide chemistry with crucial applications in pharmaceuticals, materials science, and research. Its role in protecting amino acids during synthesis allows for the precise construction of peptides, contributing to the development of therapeutic agents and advanced materials. The compound’s discovery and utilization highlight its importance in both scientific research and industrial applications.

References

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