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.
In the Vinony graph
Vinony's link graph records 16 inbound references to diglycine, and connects out to International Standard Book Number, pH and digital object identifier.
Vinony files it under Chembox having GHS data, Chembox image size set and Dimers (chemistry).
Vinony links it to 12 Wikipedia language editions.
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.