L-tert-Leucine
[CAS# 20859-02-3]

Identification

• Classification: Biochemical >> Common amino acids and protein drugs
• Name: L-tert-Leucine
• Synonyms: L-2-Amino-3,3-dimethylbutanoic acid
• Molecular Formula: C₆H₁₃NO₂
• Molecular Weight: 131.17
• Protein Sequence: X
• CAS Registry Number: 20859-02-3
• EC Number: 606-659-6
• SMILES: CC(C)(C)[C@@H](C(=O)O)N

Properties

• Density: 1.0±0.1 g/cm³, Calc.^*
• Melting point: 316 °C (Expl.)
• alpha: 6.3 ° (c=4, 6 N HCl 200 °C) (Expl.)
• Index of Refraction: 1.464, Calc.^*
• Boiling Point: 217.7±23.0 °C (760 mmHg), Calc.^*
• Flash Point: 85.5±22.6 °C, Calc.^*
• Water solubility: 125.5 g/L (20 °C)

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H315-H319-H335
• Safety Statements: P261-P264-P264+P265-P271-P280-P302+P352-P304+P340-P305+P351+P338-P319-P321-P332+P317-P337+P317-P362+P364-P403+P233-P405-P501

Discovery and Applications

L-tert-Leucine is a branched-chain amino acid that plays an important role in various biochemical processes and has a wide range of applications, particularly in pharmaceutical and chemical industries. It is an enantiomer of tert-leucine, which is commonly used in peptide synthesis, protein engineering, and as a chiral auxiliary in organic synthesis. The structure of L-tert-leucine features a leucine backbone with a bulky tert-butyl group attached to the α-carbon, which contributes to its steric properties and functionality.

The discovery of L-tert-leucine arose from ongoing research into amino acids and their potential applications in synthetic chemistry. Leucine, a naturally occurring essential amino acid, has been well studied for its role in protein synthesis and metabolism. The specific variant, L-tert-leucine, was developed to offer distinct steric hindrance, making it useful in synthetic routes where traditional leucine might not be as effective. The tert-butyl group, which is attached to the side chain of the amino acid, makes it particularly valuable in the formation of stable intermediates for chemical reactions, as well as in the creation of specific molecular structures that require bulky substituents.

One of the primary applications of L-tert-leucine is in the synthesis of peptides and proteins. Peptides are short chains of amino acids that play key roles in biological processes, including hormone regulation, immune response, and enzyme catalysis. By incorporating L-tert-leucine into peptide chains, researchers can modify the properties of these peptides, such as their stability, activity, and binding affinity to specific targets. This is especially valuable in drug design, where custom peptides are often created to interact with specific proteins or receptors.

L-tert-leucine is also used in the preparation of chiral ligands and catalysts, where its steric properties can influence the outcome of asymmetric reactions. In organic synthesis, the presence of a bulky group like the tert-butyl group allows for selective control over reaction mechanisms, making L-tert-leucine a key tool in the development of new synthetic methodologies. The ability to control the spatial arrangement of atoms in a molecule is critical in the synthesis of complex compounds, especially when high enantiomeric purity is required.

In addition to its use in synthesis, L-tert-leucine has applications in materials science. For example, it has been employed in the design of novel materials with specific functional properties, such as catalysts for chemical reactions or materials for drug delivery systems. The combination of its structural characteristics and its ability to interact with other compounds makes L-tert-leucine an ideal candidate for use in the development of advanced materials for various industrial and medical applications.

L-tert-leucine’s role extends beyond research and development in pharmaceuticals and materials science. It has also been studied for its potential benefits in metabolic disorders and its involvement in regulating muscle protein synthesis. As an essential amino acid, leucine is involved in the mTOR pathway, which regulates cell growth and metabolism. The modification of leucine into L-tert-leucine has been explored for its potential to influence metabolic pathways, although further research is needed to fully understand its effects in biological systems.

In summary, L-tert-leucine is a versatile chemical compound with significant applications in the fields of organic synthesis, pharmaceutical development, and materials science. Its structural properties make it an important tool for researchers looking to modify peptides, design chiral catalysts, and create novel materials. As studies continue, it is likely that L-tert-leucine will find even broader applications in drug development and other areas of research.

References

2021. Transient directing ligands for selective metal-catalysed C-H activation. Nature Reviews. Chemistry, 5(1). DOI: 10.1038/s41570-021-021-00321-3

2022. Enzymatic cascade systems for D-amino acid synthesis: progress and perspectives. Systems Microbiology and Biomanufacturing DOI: 10.1007/s43393-021-00037-9

2022. Palladium-Catalyzed Oxidative Cross-Coupling of Two Alkenes Using tert-Leucine as Transient Directing Group. Synfacts. DOI: 10.1055/s-0041-1738240