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G3923

Sigma-Aldrich

Gly-Pro-Glu

≥98% (HPLC)

Synonym(s):

GPE, Glycyl-prolyl-glutamic acid

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About This Item

Empirical Formula (Hill Notation):
C12H19N3O6
CAS Number:
Molecular Weight:
301.30
MDL number:
UNSPSC Code:
12352209
PubChem Substance ID:
NACRES:
NA.32

Quality Level

Assay

≥98% (HPLC)

form

powder

color

white

storage temp.

−20°C

SMILES string

NCC(=O)N1CCC[C@H]1C(=O)N[C@@H](CCC(O)=O)C(O)=O

InChI

1S/C12H19N3O6/c13-6-9(16)15-5-1-2-8(15)11(19)14-7(12(20)21)3-4-10(17)18/h7-8H,1-6,13H2,(H,14,19)(H,17,18)(H,20,21)/t7-,8-/m0/s1

InChI key

JJGBXTYGTKWGAT-YUMQZZPRSA-N

General description

IGF1 (insulin-like growth factor 1) protein is cleaved into des-N-(1-3)-IGF-1 and an N-terminal Gly-Pro-Glu (GPE tripeptide). It is thought to be an outcome of specific neural processing.

Biochem/physiol Actions

Gly-Pro-Glu (GPE) is a neuroactive peptide and prevents the binding of glutamate to N-methyl-D-aspartate (NMDA) receptor. It positively regulates the potassium-mediated release of acetylcholine from rat cortical slices. Thus, it is involved in the control of brain function. In vitro studies show that this peptide confers neuroprotection to CA1-2 hippocampal neurons against excitotoxic insult.
Gly-Pro-Glu is a neuroprotective compound and the N-terminal tripeptide of IGF-1. Gly-Pro-Glu is neuroprotective after central administration in animal models of neurodegenerative processes, such as Huntington′s, Parkinson′s, Alzheimer′s diseases, and varies acute brain injury animal models. The neuroprotective activity is not related to its affinity to glutamate receptor. Findings indicate that GPE mimics insulin-like growth factor I effects on the somatostatin system through a mechanism independent of β-amyloid clearance that involves modulation of calcium and glycogen synthase kinase 3β signaling.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable


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SeEun Choe et al.
Pathogens (Basel, Switzerland), 9(3) (2020-03-04)
Here, we examined the pathogenicity and genetic differences between classical swine fever viruses (CSFV) isolated on pig farms in North Vietnam from 2014-2018. Twenty CSFV strains from 16 pig farms were classified as genotype 2 (sub-genotypes 2.1b, 2.1c, and 2.2).
J Guan et al.
Neuropharmacology, 47(6), 892-903 (2004-11-06)
The N-terminal tripeptide of insulin-like growth factor-1, GPE is neuroprotective when given intracerebroventricularly 2 h after hypoxic-ischemic (HI) brain injury in rats. We have now examined whether GPE can cross the blood-brain barrier and exert neuroprotective actions following intravenous administration.
Matthias Van Hul et al.
American journal of physiology. Endocrinology and metabolism, 314(4), E334-E352 (2017-09-07)
Increasing evidence suggests that polyphenols have a significant potential in the prevention and treatment of risk factors associated with metabolic syndrome. The objective of this study was to assess the metabolic outcomes of two polyphenol-containing extracts from cinnamon bark (CBE)
Nicholas S Trotter et al.
Bioorganic & medicinal chemistry, 13(2), 501-517 (2004-12-16)
The synthesis of nine GPE* analogues, wherein the alpha-carboxylic acid group of glutamic acid has been modified, is described by coupling readily accessible N-benzyloxycarbonyl-glycyl-L-proline 2 with various analogues of glutamic acid. Pharmacological evaluation of the novel compounds was undertaken to
Armelle Darrasse et al.
BMC genomics, 14, 761-761 (2013-11-08)
Xanthomonads are plant-associated bacteria responsible for diseases on economically important crops. Xanthomonas fuscans subsp. fuscans (Xff) is one of the causal agents of common bacterial blight of bean. In this study, the complete genome sequence of strain Xff 4834-R was

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