3929-61-1

Usage

Definition

ChEBI: A dipeptide composed of two L-glutamic acid units joined by a peptide linkage.

InChI:InChI=1/C10H16N2O7/c11-5(1-3-7(13)14)9(17)12-6(10(18)19)2-4-8(15)16/h5-6H,1-4,11H2,(H,12,17)(H,13,14)(H,15,16)(H,18,19)/t5-,6-/m0/s1

Upstream product

• 56-86-0 L-glutamic acid 
• 5680-86-4 N-benzyloxycarbonyl-5-O-benzyl-L-glutamic acid 
• 2791-84-6 L-glutamic acid dibenzyl ester 4-toluenesulfonate 
• 35726-62-6 (S)-2-(benzyloxycarbonylamino)-5-ethoxy-5-oxopentanoic acid 
• 3523-22-6 (2S)-2-[(2S)-2-carboxybenzylamino-4-(ethoxycarbonyl)butanoyl]aminopentanedioic acid diethyl ester 
• 657-27-2 L-Lysine hydrochloride 
• 79-14-1 glycolic Acid 
• 1118-89-4 diethyl-L-glutamate hydrochloride 
• 111586-92-6 N-(N-benzyloxycarbonyl-L-α-glutamyl)-glutamic acid 
• 6922-66-3 benzyloxycarbonyl-γ-benzyl-α-L-glutamyl-L-glutamic acid dibenzyl ester 

Downstream Products

• 29227-92-7 5-oxoprolyl-L-glutamic acid 
• 56-86-0 L-glutamic acid 

Relevant academic research and scientific papers

Ester-mediated peptide formation promoted by deep eutectic solvents: a facile pathway to proto-peptides

The ester-amide exchange reaction enables spontaneous formation of prebiotic proto-peptides under mild conditions. However, this reaction also leads to oligomers with a vast sequence diversity of ester and amide linkages. Here, we demonstrate using deep eutectic solvents as a universal strategy to regulate the reaction pathways and promote the formation of amino acid-enriched oligomers with peptide backbones.

Modelling of prebiotic synthesis and selection of peptides under isothermal conditions and thermal cycling mode

The model peptide synthesis from mixtures of amino acids was carried out under the thermal cycling and isothermal modes. The compositions of the obtained mixtures of products and the primary amino acid sequence of the synthesized peptides were determined by Fourier transform ion cyclotron resonance mass spectrometry and tandem mass spectrometry in combination with high-performance liquid chromatography with the application of de novo sequencing of the synthesized products. The processes of abiogenous synthesis of peptides were shown to occur under relatively mild temperature conditions and give a substantially less number of peptides as compared with the possible statistical set. The evolution of the system takes place in the process of the synthesis in solid phase with the disappearance of a series of the most unstable peptides. The selection process with the formation of complementary peptides takes place in peptide synthesis under the thermal cyclic mode.

The Relationship between Taste and Primary Structure of "Delicious Peptide" (Lys-Gly-Asp-Glu-Glu-Ser-Leu-Ala) from Beef Soup

"Delicious peptide" was reported to be as delicious as beef soup.The peptide and its fragments were synthesized to study its taste active sites. "Delicious peptide" was found to produce a umami and a sour taste.By preparing several di- or tripeptides composed of basic or acidic amino acids, we found that the taste of "delicious peptide" was produced by an interaction between the basic and the acidic fragments in the peptide.

Synthesis of γ-Glutamyl Peptides Catalyzed by Transamidase from Bacillus natto

Crude ammonium sulfate fraction of a cell free extract from Bacillus natto contained an enzyme (or enzymes) which catalyzed the transamidation reaction specific for glutamine.Both L- and D-isomers of glutamine were active as substrate.On incubation of L- or D-glutamine with the enzyme preparation, two peptides consisting of glutamic acid and glutamine were formed.The main component of the peptides was readily isolated by ion-exchange chromatography and identified as γ-glutamylglutamine by paper chromatography and by paper electrophoresis using authentic peptides.The optical configuration of the amino acid residues in the dipeptide was determined by digestion of the acid hydrolyzate with L-glutamic acid decarboxylase, and the result showed that the dipeptide obtained from L-glutamine was a L-L isomer, while the dipeptide from D-glutamine was a D-D isomer.