gamma-Glutamylphenylalanine

(2S)-2-Amino-4-{[(1S)-1-carboxy-2-phenylethyl]carbamoyl}butanoic acid

Formula: C14H18N2O5 (294.1216)
Chinese Name: γ-谷氨酰苯丙氨酸
BioDeep ID: BioDeep_00000018623 ( View LC/MS Profile)
SMILES: N[C@@H](CCC(=O)N[C@@H](CC1=CC=CC=C1)C(O)=O)C(O)=O

Found 3 Sample Hits

m/z Adducts Species Organ Scanning Sample

m/z	Adducts	Species	Organ	Scanning	Sample
294.1453	[M-H2O+NH4]+ `PPM:1.6`	Homo sapiens	esophagus	DESI ()	LNTO22_1_4 - MTBLS385 Resolution: 17μm, 82x80 Description
295.1308	[M+H]+ `PPM:6.6`	Mus musculus	Liver	MALDI (CHCA)	Salmonella_final_pos_recal - MTBLS2671 Resolution: 17μm, 691x430 Description A more complete and holistic view on host–microbe interactions is needed to understand the physiological and cellular barriers that affect the efficacy of drug treatments and allow the discovery and development of new therapeutics. Here, we developed a multimodal imaging approach combining histopathology with mass spectrometry imaging (MSI) and same section imaging mass cytometry (IMC) to study the effects of Salmonella Typhimurium infection in the liver of a mouse model using the S. Typhimurium strains SL3261 and SL1344. This approach enables correlation of tissue morphology and specific cell phenotypes with molecular images of tissue metabolism. IMC revealed a marked increase in immune cell markers and localization in immune aggregates in infected tissues. A correlative computational method (network analysis) was deployed to find metabolic features associated with infection and revealed metabolic clusters of acetyl carnitines, as well as phosphatidylcholine and phosphatidylethanolamine plasmalogen species, which could be associated with pro-inflammatory immune cell types. By developing an IMC marker for the detection of Salmonella LPS, we were further able to identify and characterize those cell types which contained S. Typhimurium. [dataset] Nicole Strittmatter. Holistic Characterization of a Salmonella Typhimurium Infection Model Using Integrated Molecular Imaging, metabolights_dataset, V1; 2022. https://www.ebi.ac.uk/metabolights/MTBLS2671.
295.1316	[M+H]+ `PPM:9.3`	Homo sapiens	colorectal adenocarcinoma	DESI ()	520TopL, 490TopR, 510BottomL, 500BottomR-profile - MTBLS415 Resolution: 17μm, 147x131 Description The human colorectal adenocarcinoma sample was excised during a surgical operation performed at the Imperial College Healthcare NHS Trust. The sample and procedures were carried out in accordance with ethical approval (14/EE/0024).

294.1453

[M-H2O+NH4]+
PPM:1.6

Homo sapiens

esophagus

DESI ()

LNTO22_1_4 - MTBLS385

Resolution: 17μm, 82x80

Description

295.1308

[M+H]+
PPM:6.6

Mus musculus

Liver

MALDI (CHCA)

Salmonella_final_pos_recal - MTBLS2671

Resolution: 17μm, 691x430

Description

A more complete and holistic view on host–microbe interactions is needed to understand the physiological and cellular barriers that affect the efficacy of drug treatments and allow the discovery and development of new therapeutics. Here, we developed a multimodal imaging approach combining histopathology with mass spectrometry imaging (MSI) and same section imaging mass cytometry (IMC) to study the effects of Salmonella Typhimurium infection in the liver of a mouse model using the S. Typhimurium strains SL3261 and SL1344. This approach enables correlation of tissue morphology and specific cell phenotypes with molecular images of tissue metabolism. IMC revealed a marked increase in immune cell markers and localization in immune aggregates in infected tissues. A correlative computational method (network analysis) was deployed to find metabolic features associated with infection and revealed metabolic clusters of acetyl carnitines, as well as phosphatidylcholine and phosphatidylethanolamine plasmalogen species, which could be associated with pro-inflammatory immune cell types. By developing an IMC marker for the detection of Salmonella LPS, we were further able to identify and characterize those cell types which contained S. Typhimurium. [dataset] Nicole Strittmatter. Holistic Characterization of a Salmonella Typhimurium Infection Model Using Integrated Molecular Imaging, metabolights_dataset, V1; 2022. https://www.ebi.ac.uk/metabolights/MTBLS2671.

295.1316

[M+H]+
PPM:9.3

Homo sapiens

colorectal adenocarcinoma

DESI ()

520TopL, 490TopR, 510BottomL, 500BottomR-profile - MTBLS415

Resolution: 17μm, 147x131

Description

The human colorectal adenocarcinoma sample was excised during a surgical operation performed at the Imperial College Healthcare NHS Trust. The sample and procedures were carried out in accordance with ethical approval (14/EE/0024).

gamma-Glutamylphenylalanine is a dipeptide composed of gamma-glutamate and phenylalanine, and is a proteolytic breakdown product of larger proteins. It is probably formed by transpeptidation between glutathione and the corresponding amino acid, catalyzed by gamma-glutamyl transpeptidase (PMID: 237763). gamma-Glutamylphenylalanine belongs to the family of N-acyl-alpha amino acids and derivatives. These are compounds containing an alpha amino acid which bears an acyl group at its terminal nitrogen atom. gamma-Glutamylphenylalanine is an incomplete breakdown product of protein digestion or protein catabolism. Some dipeptides are known to have physiological or cell-signaling effects although most are simply short-lived intermediates on their way to specific amino acid degradation pathways following further proteolysis. It can be detected in the urine of patients with phenylketonuria, which is a human genetic disorder due to the lack of phenylalanine hydroxylase to metabolize phenylalanine to tyrosine (Wikipedia). gamma-Glutamylphenylalanine is found in adzuki bean, onion (Allium cepa), garlic (Allium sativum), and soybean. γ-Glu-Phe (γ-Glutamylphenylalanine) is synthesized by Bacillus amyloliquefaciens (GBA) and Aspergillus oryzae (GAO). γ-Glu-Phe or the post-enzymatic reaction mixture enhances the umami intensity of commercial soy sauce and model chicken broth[1]. γ-Glu-Phe (γ-Glutamylphenylalanine) is synthesized by Bacillus amyloliquefaciens (GBA) and Aspergillus oryzae (GAO). γ-Glu-Phe or the post-enzymatic reaction mixture enhances the umami intensity of commercial soy sauce and model chicken broth[1].