32302-76-4

Basic information

• Product Name: glycyl-prolyl-glutamic acid
• Synonyms: glycyl-prolyl-glutamic acid;SC-252859;L-GlutaMic acid, glycyl-L-prolyl-
• CAS NO: 32302-76-4
• Molecular Formula: C12H19N3O6
• Molecular Weight: 301.3
• Mol File: 32302-76-4.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 675.7°Cat760mmHg
• Flash Point: 362.4°C
• Appearance: /
• Density: 1.431g/cm³
• Vapor Pressure: 5.14E-20mmHg at 25°C
• Refractive Index: 1.571
• Storage Temp.: Store at 0°C
• Solubility: H2O: >5mg/mL
• CAS DataBase Reference: glycyl-prolyl-glutamic acid(CAS DataBase Reference)
• NIST Chemistry Reference: glycyl-prolyl-glutamic acid(32302-76-4)
• EPA Substance Registry System: glycyl-prolyl-glutamic acid(32302-76-4)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 32302-76-4(Hazardous Substances Data)

Usage

General Description

Glycyl-prolyl-glutamic acid, also known as GPE, is a tripeptide consisting of the amino acids glycine, proline, and glutamic acid. It plays a key role in collagen synthesis and wound healing due to its ability to promote the production of collagen and elastin in the skin. GPE has been studied for its potential anti-aging and skin-rejuvenating properties, and is often included in skincare products and cosmetics. In addition to its skincare benefits, GPE has also been studied for its potential in promoting hair growth and reducing oxidative stress. Its antioxidant properties make it a promising ingredient for protecting the skin from environmental damage and aging. Overall, GPE is a versatile compound with potential applications in skincare and haircare products.

InChI:InChI=1/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

Upstream product

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• 1160-54-9 (2S)-1-(2-[[(benzyloxy)carbonyl]amino]acetyl)tetrahydro-1H-pyrrole-2-carboxylic acid 
• 147-85-3 L-proline 
• 66449-90-9 (2S)-N-(N-Benzyloxycarbonylglycyl)proline methyl ester 
• 841233-65-6 dibenzyl N-(N-benzyloxycarbonyl-glycyl)-L-prolyl-L-glutamate 
• 47376-46-5 D-glutamic acid dibenzyl ester 
• 841233-89-4 dibenzyl N-[N-(N-benzyloxycarbonyl-glycyl)-L-prolyl]-D-glutamate 
• 37784-17-1 N-(tert-butoxycarbonyl)-D-proline 
• 853400-85-8 (R)-2-[((R)-Pyrrolidine-2-carbonyl)-amino]-pentanedioic acid dibenzyl ester 

Relevant articles and documents

A sustainable strategy for the assembly of Glypromate? and its structurally-related analogues by tandem sequential peptide coupling

This work describes an improved and greener methodology of solution-phase synthesis for the preparation of Glypromate? (glycyl-l-prolyl-l-glutamic acid, GPE), a potent neuropeptide for applications in neurodegenerative conditions such as Huntington's, Parkinson's and Alzheimer's diseases. This protocol comprises the assembly of the perbenzylated form of Glypromate? [Cbz-Gly-Pro-Glu(OBn)-OBn (5)] froml-proline. Following a tandem sequential peptide coupling strategy, two chemoselective peptide bonds are formed without the need for purifying the intermediates ensuing a one-pot fashion synthesis. EcoScale score and E-factor were selected as the green metrics to assess the environmental impact of the preparation of tripeptide5using this protocol. After optimization and application of greener conditions, intermediate5was obtained with 95percent global yield and 99percent purity (NMR, HRMS, and rp-HPLC), with excellent final EcoScale score of 75 out of 100 and global E-factor of 1.8. Glypromate? is achieved by removing N- and C-protecting groups by hydrogenolysis using Pd/C as the catalyst in 98percent yield, avoiding chromatographic techniques. Moreover, the protocol ensures stereochemical integrity (determined by VT-NMR and rp-HPLC) and was also successfully applied for the preparation of structurally-related Glypromate? analogues with higher degree of molecular complexity compatible with functionalized amino acids with different side chains. For the first time a one-pot protocol for the assembly of tripeptides with the removal of protecting groups in the same reaction vessel is reported.

Synthesis and neuroprotective activity of analogues of glycyl-L-prolyl-L- glutamic acid (GPE) modified at the α-carboxylic acid

The synthesis of nine GPE* analogues, wherein the α-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 further understand the role of the glutamate residue on the observed neuroprotective properties of the endogenous tripeptide GPE.