D-Glutamic acid 5-phenylmethyl ester
[CAS# 2578-33-8]

Identification

• Classification: Biochemical >> Amino acids and their derivatives >> Glutamic acid derivative
• Name: D-Glutamic acid 5-phenylmethyl ester
• Synonyms: D-Glutamic acid gamma-benzyl ester; gamma-Benzyl D-glutamate
• Molecular Formula: C₁₂H₁₅NO₄
• Molecular Weight: 237.26
• Protein Sequence: X
• CAS Registry Number: 2578-33-8
• EC Number: 607-810-9
• SMILES: C1=CC=C(C=C1)COC(=O)CC[C@H](C(=O)O)N

Properties

• Density: 1.2±0.1 g/cm³ Calc.^*
• Melting point: 158 °C (Expl.)
• Boiling point: 426.1±45.0 °C 760 mmHg (Calc.)^*
• Flash point: 211.5±28.7 °C (Calc.)^*
• Index of refraction: 1.555 (Calc.)^*

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

Safety Data

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

Hazard Classification

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

Discovery and Applications

D-Glutamic acid 5-phenylmethyl ester is a chemically modified derivative of D-glutamic acid, in which the carboxyl group at the fifth carbon position is esterified with a phenylmethyl group, commonly known as a benzyl group. This modification results in an ester that retains the stereochemical configuration of D-glutamic acid while introducing new chemical properties through the benzyl ester moiety.

The synthesis of D-glutamic acid 5-phenylmethyl ester typically involves the reaction of D-glutamic acid with benzyl alcohol under acidic conditions or by using coupling agents that facilitate ester formation. The presence of the benzyl ester protects the carboxyl group, making this compound valuable as an intermediate in peptide synthesis and other organic transformations where selective protection of functional groups is required.

The discovery and utilization of D-glutamic acid derivatives, including the 5-phenylmethyl ester, have been crucial in the fields of biochemistry and pharmaceutical chemistry. D-glutamic acid itself is an important component of bacterial cell walls, especially in the peptidoglycan layer, and its derivatives are used to study enzyme mechanisms and develop antibiotics. The benzyl ester form allows for controlled manipulation and incorporation into peptides or other bioactive molecules without interference from the free carboxyl group.

In practical applications, D-glutamic acid 5-phenylmethyl ester serves primarily as a protected amino acid in solid-phase peptide synthesis. The benzyl ester protects the carboxyl end during peptide chain elongation and can later be removed under specific hydrogenolysis conditions, yielding the free acid. This selective protection strategy is essential for synthesizing peptides with precise sequences and functionalities.

Beyond peptide chemistry, this compound is used in research to probe enzymatic reactions involving glutamic acid derivatives and to design molecules with potential therapeutic properties. The ester modification enhances the molecule’s lipophilicity, which can improve cell permeability in certain contexts, making it useful in drug development and delivery studies.

Due to the benzyl ester’s chemical nature, D-glutamic acid 5-phenylmethyl ester must be handled with care to avoid premature hydrolysis or unintended side reactions. It is typically stored under conditions that minimize exposure to moisture and strong acids or bases, which can cleave the ester bond.

Overall, D-glutamic acid 5-phenylmethyl ester plays a significant role as a synthetic intermediate and protective derivative in chemical and biochemical research. Its discovery and application have facilitated advances in peptide synthesis, enzymology, and drug design, contributing to the broader understanding and utilization of amino acid derivatives in science and medicine.

References

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