Compound: Glycylglycine
SMILES: O=C(O)CNC(=O)CN
InChIKey: YMAWOPBAYDPSLA-UHFFFAOYSA-N
Synonyms: Glycylglycine, 556-50-3, Diglycine, N-GLYCYLGLYCINE, Glycine, glycyl-, Glycine dipeptide, Glycyl-glycine, 2-[(2-aminoacetyl)amino]acetic acid, 2-(Aminoacetamido)acetic acid, Gly2, Glycyl Glycine, NSC-49346, 10525P22U0, CHEBI:17201, DTXSID90862194, 2-((2-aminoacetyl)amino)acetic acid, N Glycylglycine, RefChem:663940, Hydrochloride, Glycylglycine, Monohydrochloride, Glycylglycine, DTXCID80197700, 2-((2-azaniumylacetyl)amino)acetate, 2-(glycylamino)acetic acid;hydrochloride, 209-127-8, Gly-Gly, 2-(2-Aminoacetamido)Acetic Acid, H-Gly-Gly-OH, Glycylglyine, Glycine, N-glycyl-, Gly-Gly-OH, alpha-Glycylglycine, Diglycine (VAN), Glycylgycine, [(Aminoacetyl)amino]acetic acid, MFCD00008130, CHEMBL292467, [(ammonioacetyl)amino]acetate, 2-(2-azanylethanoylamino)ethanoic acid, Dipeptide-15, ((aminoacetyl)amino)acetic acid, 2-(2-aminoacetylamino)acetic acid, 2-[(2-Aminoacetyl)amino]acetic Acid (Diglycine; N-Glycylglycine), UNII-10525P22U0, GG0, EINECS 209-127-8, H-Gly-Gly, Glycylglycine, DL-, NSC 49346, .alpha.-Glycylglycine, n-GLYCYL- Glycine, AI3-62521, Glycylglycine (Standard), Glycylglycine, Free Base, Gly-Gly, 98%, GLYCYLGLYCINE [MI], DIGLYCINE [USP-RS], SCHEMBL14934, orb1301921, SCHEMBL2305997, 2-(2-Aminoacetamido)AceticAcid, HY-D0889R, Gly-Gly, >=99% (titration), [(Aminoacetyl)amino]acetic acid #, HY-D0889, NSC49346, BBL018705, BDBM50169222, EBC-44071, MSK001339, s4810, SBB067231, STL194277, AKOS001045997, 3-Azapentanoic acid, 5-amino-4-oxo-, CCG-231053, FG40134, Gly-Gly, BioXtra, >=99.0% (NT), AS-14771, BP-31104, Gly-Gly, BioUltra, >=99.5% (NT), ST099026, SY018005, Gly-Gly, Vetec(TM) reagent grade, 99%, DB-002742, Glycylglycine(Discontinued,SeeCPTD788380), CS-0015211, G0124, NS00013721, EN300-34095, C02037, F17229, G-6001, F047801, Q665455, Glycyl-glycine; N-Glycylglycine; Diglycine; Gly-Gly, 2-(2-Aminoacetamido)Acetic Acid; Glycine EP Impurity H, F2191-0195, 33903968-DDB2-47F2-9B6C-7C232D1962DA, Dyglycine, United States Pharmacopeia (USP) Reference Standard, Gly-Gly, BioPerformance Certified, cell culture tested, >=99%, InChI=1/C4H8N2O3/c5-1-3(7)6-2-4(8)9/h1-2,5H2,(H,6,7)(H,8,9
Theoretical properties:
molecular_formula: C4H8N2O3
molecular_weight: 132.12 g/mol
exact_mass: 132.05349212 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 3
hydrogen_bond_acceptor_count: 4
rotatable_bond_count: 3
heavy_atom_count: 9
topological_polar_surface_area: 92.4 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
melting_point: 215 °C
solubility: 166 mg/mL at 21 °C
vapor_pressure: 0.00000005 [mmHg]
Descriptions:
pubchem: Glycylglycine is a dipeptide formed from glycine residues. It has a role as a human metabolite. It is functionally related to a glycine. It is a tautomer of a glycylglycine zwitterion.
chebi: A dipeptide formed from glycine residues.
chembl: Unnamed Compound is a small molecule listed in the ChEMBL database but has not progressed to an approved clinical phase.
wikipedia: Glycylglycine is the dipeptide of glycine, making it the simplest peptide.
The compound was first synthesized by Emil Fischer and Ernest Fourneau in 1901 by boiling 2,5-diketopiperazine (glycine anhydride) with hydrochloric acid.
Shaking with alkali and other synthesis methods have been reported.
Because of its low toxicity, it is useful as a buffer for biological systems with effective ranges between pH 2.5–3.8 and 7.5–8.9; however, it is only moderately stable for storage once dissolved. It is used in the synthesis of more complex peptides.
Glycylglycine has also been reported to be helpful in solubilizing recombinant proteins in E. coli. Using different concentrations of the glycylglycine improvement in protein solubility after cell lysis has been observed.