32302-76-4

Usage

Uses

Used in Skincare Industry:
Glycyl-prolyl-glutamic acid is used as an active ingredient for its skin-rejuvenating and anti-aging properties, as it promotes collagen and elastin production, enhancing skin elasticity and reducing the appearance of fine lines and wrinkles.
Used in Haircare Industry:
Glycyl-prolyl-glutamic acid is used as a hair growth promoter, potentially stimulating hair follicle health and contributing to thicker, fuller hair.
Used in Antioxidant Formulations:
Glycyl-prolyl-glutamic acid is used as an antioxidant in skincare and haircare products to protect against environmental stressors and oxidative damage, thus preserving the health and appearance of the skin and hair.
Used in Wound Healing Applications:
Glycyl-prolyl-glutamic acid is used as a component in wound healing formulations to facilitate the repair process by enhancing collagen synthesis, which is essential for tissue regeneration and recovery.

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

• 29022-11-5 N-(fluoren-9-ylmethoxycarbonyl)glycine 
• 71989-31-6 (R)-Pyrrolidine-1,2-dicarboxylic acid 1-(9H-fluoren-9-ylmethyl) ester 
• 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 academic research and scientific papers

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.

DPP-4 inhibitor

A DPP-4 inhibitor comprising a peptide represented by the formula (1): Xe-Pro/Ala/Hyp-Xa-Xb-Xc-Xd (SEQ ID NO: 16) (wherein Xe is an amino acid residue with an isoelectric point of 5.9 to 6.3; Pro/Ala/Hyp represents Pro, Ala, or Hyp; Xa is an amino acid residue other than Hyp, Pro, and Arg, or deletion; 5 Xb is Gly, Pro, or deletion; Xc is Pro, Ala, or deletion; and Xd is an amino acid residue or deletion) as an active component. The inhibitor can be expected to bring out an effect of lowering blood glucose levels by enhancing effects of incretins; and the inhibitor may be used as a therapeutic agent for diabetes and, in addition, can act on the immune system or the like to be thus used in 10 treatment for skin diseases or the like.

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.

Analogues of the neuroprotective tripeptide Gly-Pro-Glu (GPE): Synthesis and structure-activity relationships

A series of GPE analogues, including modifications at the Pro and/or Glu residues, was prepared and evaluated for their NMDA binding and neuroprotective effects. Main results suggest that the pyrrolidine ring puckering of the Pro residue plays a key role