Methoxycarbonyl-L-tert-leucine
[CAS# 162537-11-3]

Identification

• Classification: Biochemical >> Amino acids and their derivatives >> Leucine derivative
• Name: Methoxycarbonyl-L-tert-leucine
• Synonyms: (S)-2-Methoxycarbonylamino-3,3-dimethylbutyric acid
• Molecular Formula: C₈H₁₅NO₄
• Molecular Weight: 189.21
• Protein Sequence: X
• CAS Registry Number: 162537-11-3
• EC Number: 605-292-9
• SMILES: CC(C)(C)[C@@H](C(=O)O)NC(=O)OC

Properties

• Density: 1.1±0.1 g/cm³, Calc.^*
• Melting point: 107-110 °C (Expl.)
• Index of Refraction: 1.460, Calc.^*
• Boiling Point: 320.9±25.0 °C (760 mmHg), Calc.^*
• Flash Point: 147.9±23.2 °C, Calc.^*

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

Safety Data

• Hazard Symbols: GHS05 Danger
• Risk Statements: H318-H412
• Safety Statements: P264+P265-P273-P280-P305+P354+P338-P317-P501

Discovery and Applications

Methoxycarbonyl-L-tert-leucine is a derivative of the naturally occurring amino acid leucine, featuring a methoxycarbonyl group attached to the amino group of the L-tert-leucine structure. This compound is of interest in the fields of organic chemistry, biochemistry, and medicinal chemistry due to its potential applications in peptide synthesis, drug design, and various other therapeutic applications.

The discovery of methoxycarbonyl-L-tert-leucine is part of ongoing efforts to synthesize modified amino acids that can be used to enhance the stability, selectivity, and efficacy of peptides and proteins. Leucine, an essential branched-chain amino acid, plays a crucial role in protein synthesis and cellular metabolism. By introducing the methoxycarbonyl group at the nitrogen atom of L-tert-leucine, researchers are able to modify the amino acid to serve as a more versatile building block for peptides and other bioactive compounds.

Methoxycarbonylation of amino acids such as L-leucine is a common strategy in peptide chemistry to protect the amino group during the synthesis of peptides. The methoxycarbonyl group serves as a temporary protective group, allowing for the construction of complex peptide sequences without interference from the amino group. Once the peptide chain has been assembled, the protecting group can be removed under mild conditions, thus yielding the desired peptide or protein with minimal side reactions. This feature makes methoxycarbonyl-L-tert-leucine a valuable intermediate in peptide synthesis.

Additionally, methoxycarbonyl-L-tert-leucine has potential applications in drug discovery and the development of therapeutics. The modification of amino acids can impart specific chemical properties to peptides, enhancing their bioavailability, stability, and resistance to enzymatic degradation. In particular, the tert-butyl group in L-tert-leucine adds steric bulk, which can influence the conformation and folding of peptides, making them more suitable for targeting specific biological pathways or receptors. This modification has led to the development of peptide-based drugs with improved pharmacokinetic profiles and reduced immunogenicity.

Beyond its use in peptide synthesis, methoxycarbonyl-L-tert-leucine has been explored as a potential tool for designing enzyme inhibitors and other small molecule drugs. By incorporating modified amino acids like methoxycarbonyl-L-tert-leucine into the structures of biologically active compounds, researchers can achieve greater specificity and potency in targeting particular enzymes or receptors involved in disease processes.

The compound has also attracted interest in the development of protein-protein interaction inhibitors. Proteins often interact through specific binding domains, and peptides that mimic these domains can be used to disrupt interactions involved in disease mechanisms, such as cancer metastasis or viral infections. Methoxycarbonyl-L-tert-leucine, as a versatile building block, can contribute to the design of such peptide-based inhibitors.

In conclusion, methoxycarbonyl-L-tert-leucine is a valuable compound in the field of medicinal chemistry and peptide synthesis. Its protective group functionality, combined with the steric influence of the tert-butyl group, makes it an important building block for the design of bioactive peptides and small molecules. As research into the modification of amino acids continues, methoxycarbonyl-L-tert-leucine is expected to play a key role in the development of new therapeutic agents targeting a variety of diseases.

References

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DOI: 10.1007/s11419-018-0415-z

2006. Atazanavir sulfate. Pharmaceutical Substances.
URL: https://pharmaceutical-substances.thieme.com/ps/search-results?docUri=KD-01-0164