glycyl-prolyl-glutamic acid

Base Information

• Chemical Name: glycyl-prolyl-glutamic acid
• CAS No.: 32302-76-4
• Molecular Formula: C₁₂H₁₉N₃O₆
• Molecular Weight: 301.299
• UNII: ZYK4RVV5LS
• DSSTox Substance ID: DTXSID80186038
• Nikkaji Number: J556.653C
• Wikidata: Q72507092
• Metabolomics Workbench ID: 82142
• ChEMBL ID: CHEMBL371315
• Mol file: 32302-76-4.mol

Synonyms:Glutamicacid, N-(1-glycyl-L-prolyl)-, L- (8CI); L-Glutamic acid,N-(1-glycyl-L-prolyl)-; (1-3)-Human insulin-like growth factor I; insulin-likegrowth factor-1 N-terminal tripeptide

Chemical Property of glycyl-prolyl-glutamic acid

Chemical Property:

• Vapor Pressure: 5.14E-20mmHg at 25°C
• Boiling Point: 675.7°Cat760mmHg
• Flash Point: 362.4°C
• PSA: 153.52000
• Density: 1.431g/cm³
• LogP: -0.15120
• Storage Temp.: Store at 0°C
• Solubility.: H2O: >5mg/mL
• XLogP3: -5.1
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 7
• Exact Mass: 301.12738533
• Heavy Atom Count: 21
• Complexity: 439

Purity/Quality:

98%Min ^*data from raw suppliers

Gly-Pro-Glu ≥98% (HPLC) ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CC(N(C1)C(=O)CN)C(=O)NC(CCC(=O)O)C(=O)O
• Isomeric SMILES: C1C[C@H](N(C1)C(=O)CN)C(=O)N[C@@H](CCC(=O)O)C(=O)O
• Recent EU Clinical Trials: Assessment of the Maximal Tolerated Dose of a Microencapsulated Grass (Phleum pratense) Pollen Extract (MGPE) in Subjects with Grass Pollen Allergy in a Randomized, Double-Blind, Placebo-Controlled Study
• General Description: Glycyl-prolyl-glutamic acid (GPE) is a neuroprotective tripeptide whose activity depends on the structural conformation of its proline residue, particularly the pyrrolidine ring puckering, while the cis/trans configuration of the Gly-Pro peptide bond is less critical. Modifications to the Pro and Glu residues, such as incorporating (S)-α-methylproline (PMe) or LL-5,5-dimethylproline (dmP), can enhance NMDA receptor binding and neuroprotective effects, indicating that the Gly-Pro amide bond conformation is not essential for receptor interaction. These findings highlight the importance of Pro residue flexibility in mediating GPE's biological activity.

Technology Process of glycyl-prolyl-glutamic acid

There total 17 articles about glycyl-prolyl-glutamic acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 98.0%

dibenzyl N-(N-benzyloxycarbonyl-glycyl)-L-prolyl-L-glutamate (841233-65-6) → Gly-Pro-Glu (32302-76-4)

Guidance literature:

With palladium 10% on activated carbon; hydrogen; In methanol; water; at 20 ℃; for 4h; under 3102.97 Torr; Darkness; Green chemistry;

DOI:10.1039/d0gc00143k

Reference yield: 94.0%

dibenzyl N-[N-(N-benzyloxycarbonyl-glycyl)-L-prolyl]-D-glutamate (841233-89-4) → H-Gly-Pro-D-Glu-OH (32302-76-4)

Guidance literature:

With hydrogen; palladium on activated charcoal; In methanol; water; at 20 ℃;

DOI:10.1016/j.bmc.2004.10.005

Reference yield:

C24H26NO5Pol + N-(fluoren-9-ylmethoxycarbonyl)glycine (29022-11-5) + (R)-Pyrrolidine-1,2-dicarboxylic acid 1-(9H-fluoren-9-ylmethyl) ester (71989-31-6,109425-54-9,144829-96-9,101555-62-8) → Gly-Pro-Glu (32302-76-4)

Guidance literature:

C₂₄H₂₆NO₅Pol; With piperidine; In N,N-dimethyl-formamide; for 0.166667h; Wang resin

(R)-Pyrrolidine-1,2-dicarboxylic acid 1-(9H-fluoren-9-ylmethyl) ester; With benzotriazol-1-ol; diisopropyl-carbodiimide; In N,N-dimethyl-formamide; for 1h; Wang resin

N-(fluoren-9-ylmethoxycarbonyl)glycine; Further stages;

upstream raw materials:

(R)-2-[((R)-Pyrrolidine-2-carbonyl)-amino]-pentanedioic acid dibenzyl ester

D-glutamic acid dibenzyl ester

N-(tert-butoxycarbonyl)-D-proline

dibenzyl N-[N-(N-benzyloxycarbonyl-glycyl)-L-prolyl]-D-glutamate

Refernces

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

10.1016/j.bmcl.2005.03.015

The research investigates the synthesis and structure–activity relationships of analogues of the neuroprotective tripeptide Gly-Pro-Glu (GPE). The study focuses on modifications at the Pro and/or Glu residues to explore their effects on NMDA binding and neuroprotective properties. Key chemicals involved include Boc- and tBu-protected Gly and Glu for the synthesis of certain analogues, as well as various proline derivatives such as 2,2-dimethyl-thiazolidine-4(R)-carboxylic acid (Cys[ΨMe,Mepro]) and (S)-α-methylproline (PMe). Other significant compounds used are LL-5,5-dimethylproline (dmP) and different stereoisomeric forms of GPE incorporating D-configurations and analogues containing aspartic or homoglutamic (Hgl) acid. The study found that the pyrrolidine ring puckering of the Pro residue is crucial for biological activity, while the preference for cis or trans rotamers around the Gly-Pro peptide bond is not significant. Compounds 4 and 5, incorporating PMe and dmP respectively, showed notable affinity for GluRs and neuroprotective effects, suggesting that the Gly-Pro amide conformation is not essential for interaction with the NMDA receptor.