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L-alpha-Glutamyl-L-Alanine
[CAS# 21064-18-6]

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Identification
Classification Biochemical >> Peptide
Name L-alpha-Glutamyl-L-Alanine
Synonyms H-Glu-Ala-OH; (4S)-4-amino-5-[[(1S)-1-carboxyethyl]amino]-5-oxopentanoic acid
Molecular Structure CAS # 21064-18-6, L-alpha-Glutamyl-L-Alanine, H-Glu-Ala-OH, (4S)-4-amino-5-[[(1S)-1-carboxyethyl]amino]-5-oxopentanoic acid
Protein Sequence EA
Molecular Formula C8H14N2O5
Molecular Weight 218.21
CAS Registry Number 21064-18-6
SMILES C[C@@H](C(=O)O)NC(=O)[C@H](CCC(=O)O)N
Properties
Density 1.4±0.1 g/cm3 Calc.*
Boiling point 566.5±50.0 ºC 760 mmHg (Calc.)*
Flash point 296.4±30.1 ºC (Calc.)*
Index of refraction 1.528 (Calc.)*
* Calculated using Advanced Chemistry Development (ACD/Labs) Software.
Safety Data
Hazard Symbols symbol   GHS07 Warning    Details
Hazard Statements H302-H312-H332    Details
Precautionary Statements P261-P264-P270-P271-P280-P301+P312-P302+P352-P304+P340-P330-P363-P501    Details
SDS Available
up Discovory and Applicatios
H-Glu-Ala-OH is a dipeptide consisting of L-glutamic acid (Glu) and L-alanine (Ala) linked through a peptide bond, with free amino and carboxyl termini. This simple dipeptide belongs to the large class of short peptides that have been widely studied as fundamental models for understanding peptide structure, stability, and biological function. Its systematic representation reflects the free α-amino group at the N-terminus (H–) and the free carboxyl group at the C-terminus (–OH).

The discovery of dipeptides like H-Glu-Ala-OH is rooted in the early 20th-century studies on protein hydrolysis. When scientists such as Emil Fischer and his contemporaries investigated the breakdown products of proteins, they identified dipeptides and tripeptides as intermediate units that revealed how amino acids were linked together in polypeptide chains. H-Glu-Ala-OH, as one of the possible fragments of larger proteins, has been found in enzymatic hydrolysates of dietary proteins. The presence of glutamic acid and alanine residues in proteins is common, and short peptides containing them can result from natural proteolysis in living organisms.

Applications of H-Glu-Ala-OH and related dipeptides are diverse. In biochemical research, it is used as a model substrate in enzymology to study the specificity of proteases and peptidases, which recognize and cleave short peptide sequences. The dipeptide is particularly useful for probing enzyme activity because the side chains of glutamic acid and alanine provide contrasting properties: glutamic acid carries a negatively charged carboxylate side chain under physiological conditions, while alanine is a small hydrophobic residue. These differences make the peptide suitable for investigating enzyme binding preferences and catalytic mechanisms.

In pharmaceutical and nutritional sciences, short dipeptides such as H-Glu-Ala-OH are investigated for their potential bioactivity. Although simple dipeptides generally do not display strong pharmacological properties, they may influence physiological processes such as taste perception, cellular uptake of amino acids, and modulation of metabolic pathways. Peptides containing glutamic acid residues, for instance, are known to contribute to umami taste and may also act as precursors in neurotransmitter metabolism. The alanine residue contributes to structural simplicity and metabolic stability.

From a chemical perspective, H-Glu-Ala-OH is also important for studies on peptide synthesis. It is frequently used as a standard in solid-phase peptide synthesis (SPPS) and solution-phase methods, serving as a model for optimizing coupling conditions and protecting-group strategies. Its preparation involves coupling protected forms of glutamic acid and alanine followed by deprotection, which provides a straightforward demonstration of the principles of peptide bond formation. The compound is also used in chromatographic studies as a reference standard for peptide separation and identification.

In materials and food sciences, dipeptides like H-Glu-Ala-OH are explored for their role in protein-derived hydrolysates, which can impart functional properties such as antioxidant activity, metal-chelation capacity, or enhancement of food flavor. While H-Glu-Ala-OH itself is not one of the most bioactive dipeptides, its presence in protein breakdown mixtures highlights the broad spectrum of naturally occurring small peptides that can be utilized in applied research.

Overall, H-Glu-Ala-OH exemplifies how a simple dipeptide carries significance across multiple disciplines. Its discovery as a product of protein hydrolysis contributed to the understanding of protein structure, while its synthetic availability makes it a reliable model compound in peptide chemistry. Its applications range from enzymatic studies and peptide synthesis to potential roles in food science and biological research, demonstrating the broad utility of even the simplest peptide fragments.

References

1976. Enzymatic preparation of peptides of the general type: L-Ala-D-Glu + … Biochimie, 58(10).
DOI: https://doi.org/10.1016/S0300-9084(76)80115-0

2001. Dipeptide model prodrugs for the intestinal oligopeptide transporter. Affinity for and transport via hPepT1 in the human intestinal Caco-2 cell line. Journal of Controlled Release, 76(1-2).
DOI: https://doi.org/10.1016/S0168-3659(01)00427-8

2019. Synthesis of d-amino acid-containing dipeptides using enzymatic adenylation and chemical coupling. Applied and Environmental Microbiology, 85(14).
DOI: https://doi.org/10.1128/AEM.00120-19
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