L-Glutamic acid 1-tert-butyl ester
[CAS# 45120-30-7]

Identification

• Classification: Biochemical >> Amino acids and their derivatives >> Glutamic acid derivative
• Name: L-Glutamic acid 1-tert-butyl ester
• Synonyms: (4S)-4-amino-5-[(2-methylpropan-2-yl)oxy]-5-oxopentanoic acid
• Molecular Formula: C₉H₁₇NO₄
• Molecular Weight: 203.11
• Protein Sequence: E
• CAS Registry Number: 45120-30-7
• EC Number: 801-523-4
• SMILES: CC(C)(C)OC(=O)[C@H](CCC(=O)O)N

Properties

• Density: 1.1±0.1 g/cm³, Calc.^*
• Melting point: 139-145 °C
• alpha: 13
• Index of Refraction: 1.476, Calc.^*
• Boiling Point: 326.8±32.0 °C (760 mmHg), Calc.^*
• Flash Point: 151.5±25.1 °C, Calc.^*

^* 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

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Eye irritation	Eye Irrit.	2A	H319
Specific target organ toxicity - single exposure	STOT SE	3	H335
Skin irritation	Skin Irrit.	2	H315

Discovery and Applications

L-Glutamic acid 1-tert-butyl ester is an important compound in the fields of organic chemistry and biochemistry, primarily recognized for its role as an amino acid derivative. The discovery of this compound can be traced back to the growing interest in amino acid derivatives in the mid-20th century, coinciding with advancements in peptide synthesis and the development of pharmaceuticals.

The synthesis of L-glutamic acid 1-tert-butyl ester involves the reaction of L-glutamic acid with tert-butanol in the presence of an acid catalyst. This reaction results in the formation of the tert-butyl ester, which enhances the lipophilicity and stability of the amino acid. The introduction of the tert-butyl group at the carboxyl position provides a protective strategy, facilitating further modifications and synthesis of more complex molecules.

L-Glutamic acid 1-tert-butyl ester has a range of applications in synthetic organic chemistry. One of its primary uses is as a protected form of glutamic acid in peptide synthesis. The tert-butyl ester group effectively shields the carboxyl group, preventing unwanted reactions during the coupling of amino acids to form peptides. This protective strategy is crucial for maintaining the integrity of the peptide bond formation process, ultimately leading to higher yields and purities of the final peptide products.

In addition to its role in peptide synthesis, L-glutamic acid 1-tert-butyl ester is utilized in the development of various pharmaceutical compounds. The enhanced stability and solubility provided by the tert-butyl ester group make this compound an attractive intermediate for synthesizing bioactive molecules, including neuroprotective agents and pharmaceuticals targeting the central nervous system. Glutamic acid itself plays a critical role as a neurotransmitter, and derivatives like the tert-butyl ester are being investigated for their potential therapeutic effects.

Moreover, L-glutamic acid 1-tert-butyl ester is employed in the preparation of various derivatives that have been studied for their biological activity. Research indicates that modifications of glutamic acid can lead to compounds with enhanced efficacy and selectivity, making them suitable candidates for drug development. The versatility of this ester allows for the exploration of different pharmacophores, contributing to the discovery of novel therapeutic agents.

Recent advancements in the synthesis and application of L-glutamic acid derivatives highlight the compound's significance in drug design and development. Ongoing research focuses on understanding the pharmacological properties of glutamic acid esters, including their mechanisms of action and potential uses in treating neurological disorders.

In summary, L-glutamic acid 1-tert-butyl ester is a vital compound with a rich history and diverse applications in organic synthesis and pharmaceuticals. Its discovery has significantly impacted peptide synthesis methodologies, and its continued exploration underscores its importance in advancing research in medicinal chemistry and drug development.

References

2000. Evaluation of novel dendrimer chiral stationary phases using HPLC. Chromatographia, 51(3-4).
DOI: 10.1007/bf02491562