Glycylglycylglycine zwitterion

Base Information

• Chemical Name: Glycylglycylglycine zwitterion
• CAS No.: 556-33-2
• Molecular Formula: C6H11N3O4
• Molecular Weight: 189.171
• Hs Code.: 29241990
• Mol file: 556-33-2.mol

Synonyms:GGG zwitterion;Gly-Gly-Gly zwitterion;glycylglycylglycine zwitterion;CHEBI:195214;{[N-(azaniumylacetyl)glycyl]amino}acetate

Chemical Property of Glycylglycylglycine zwitterion

Chemical Property:

• Appearance/Colour: white crystalline powder
• Vapor Pressure: 5.82E-18mmHg at 25°C
• Melting Point: 240-250 °C
• Refractive Index: 1.524
• Boiling Point: 638.8 °C at 760 mmHg
• PKA: 3.225(at 25℃)
• Flash Point: 340.1 °C
• PSA: 121.52000
• Density: 1.373 g/cm³
• LogP: -1.25580
• Storage Temp.: 2-8°C
• Solubility.: H2O: 0.5 M at 20 °C, clear, colorless
• Water Solubility.: Soluble in water (94.6 mg/ml at 20°C), methanol (50 mg/ml), and 80% acetic acid (50 mg/ml).
• XLogP3: -2.9
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4
• Exact Mass: 189.07495584
• Heavy Atom Count: 13
• Complexity: 210

Purity/Quality:

99% ^*data from raw suppliers

Glycylglycylglycine >98.0%(T) ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C(C(=O)NCC(=O)NCC(=O)[O-])[NH3+]
• Uses: Substrate for tripeptide aminopeptidase. Glycyl-glycyl-glycine is used as a model peptide for studies of physicochemical parameters and molecular associations of small peptides. It is also used as a copper chelator.

Technology Process of Glycylglycylglycine zwitterion

There total 41 articles about Glycylglycylglycine zwitterion 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: 92.0%

DL-phenylalanine methyl ester (15028-44-1) + 1-O-(glycylglycylglycyl)-β-D-glucopyranose (75719-94-7) → glycine-glycine-glycine (556-33-2) + glycylglycylglycyl-D,L-phenylalanine methyl ester (84814-47-1)

Guidance literature:

With 4-methyl-morpholine; In N,N-dimethyl-formamide; at 38 ℃; for 72h;

DOI:10.1016/S0008-6215(00)81893-5

Reference yield: 90.0%

[2-(2-Benzyloxycarbonylamino-acetylamino)-acetylamino]-acetic acid (2566-20-3) → glycine-glycine-glycine (556-33-2)

Guidance literature:

With acetic acid; In methanol; Ambient temperature; electrolysis: palladium/graphite cathode, -0.6 V to -1.0 V SCE, current density = 15 mA/cm², catholyte: NaClO₄;

DOI:10.1055/s-1987-28191

Reference yield: 66.0%

tetrabutylphosphonium glycinate + glycine ethyl ester hydrochloride (5680-79-5,883886-67-7) → glycine-glycine-glycine (556-33-2)

Guidance literature:

tetrabutylphosphonium glycinate; for 3h; Inert atmosphere;

glycine ethyl ester hydrochloride; In chloroform; at 60 ℃; for 24h;

With acetic acid; In chloroform; at 20 ℃; for 10h;

DOI:10.1002/chem.201501783

upstream raw materials:

chloroacetyldiglycine

N-carboxy-glycyl=>glycyl=>glycine

[2-(2-Benzyloxycarbonylamino-acetylamino)-acetylamino]-acetic acid

DL-phenylalanine methyl ester

Downstream raw materials:

N-benzyloxycarbonylglycylglycylglycylglycine

N-benzyloxycarbonyl-L-seryl=>glycyl=>glycyl=>glycine ethyl ester

Oxalamide

glycyl-glycyl-glycine ethyl ester hydrochloride

Refernces

• 1、 Bujdak, J.,Slosiarikova, H.,Texler, N.,Schwendinger, M.,Rode, B. M.. "On the Possible Role of Montmorillonites in Prebiotic Peptide Formation". . p. 1033 - 1040. Retrieved 1994.
• 2、 Eder, Artur H.,Rode, Bernd M.. "Influence of Alkali- and Alkaline-earth-metal Cations on the 'Salt-induced Peptide Formation' Reaction". . p. 1125 - 1130. Retrieved 1994.
• 3、 Onoe, Jun,Kawai, Tomoji,Kawai, Shichio. "PEPTIDE FORMATION FROM AMINO ACID WITH PARTICULATE SEMICONDUCTOR PHOTOCATALYSTS". . p. 1667 - 1670. Retrieved 1985.
• 4、 Alharthi, Sitah,Ziora, Zyta Maria,Moyle, Peter Michael. "Optimized protocols for assessing libraries of poorly soluble sortase A inhibitors for antibacterial activity against medically-relevant bacteria, toxicity and enzyme inhibition". supporting information. . Retrieved 2021/11/30.
• 5、 -. "BENZYL COMPOUND". Paragraph 0218-0219. . Retrieved 2019/02/05.