Structure via PubChem · Public domain (PubChem)
diglycine
Sign in to saveAlso known as Gly-Gly, N-glycylglycine, glycine dipeptide, [(aminoacetyl)amino]acetic acid, Gly2, 2-(aminoacetamido)acetic acid, alpha-Glycylglycine, N-GLYCYL- Glycine
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.
Chemical data
- Formula
- C4H8N2O3
- Molecular weight
- 132.12 g/mol
- IUPAC name
- 2-[(2-aminoacetyl)amino]acetic acid
- SMILES
- C(C(=O)NCC(=O)O)N
- InChIKey
- YMAWOPBAYDPSLA-UHFFFAOYSA-N
- XLogP
- -2.9
- Polar surface area
- 92.4 Ų
- H-bond donors
- 3
- H-bond acceptors
- 4
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Molecule type
- Small molecule
via ChEMBL · EBI
Research
1,180 papers- Autohydrolysis of Diglycine-Activated Succinic Esters Boosts Cellular Uptake.Angewandte Chemie (International ed. in English) · 2023
- Systematic and quantitative assessment of the ubiquitin-modified proteome.Molecular cell · 2011
- Glycine, Diglycine, and Triglycine Exhibit Different Reactivities in the Formation and Degradation of Amadori Compounds.Journal of agricultural and food chemistry · 2022
- Diglycine Enables Rapid Intrabacterial Hydrolysis for Activating Anbiotics against Gram-negative Bacteria.Angewandte Chemie (International ed. in English) · 2019
- Recognition of the Diglycine C-End Degron by CRL2(KLHDC2) Ubiquitin Ligase.Molecular cell · 2018
via PubMed
Wikidata facts
- Mass
- 132.053
Show 4 more facts
- chemical formula
- C₄H₈N₂O₃
- canonical SMILES
- C(C(=O)NCC(=O)O)N
- isomeric SMILES
- C(/C(=N/CC(=O)O)/O)N
- found in taxon
- Escherichia coli
via Wikidata · CC0
~1 min read
Encyclopedic overview
1 sectionsContents
- References
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.
Excerpted from Wikipedia’s “diglycine” article, available under the CC BY-SA 4.0 licence.