Glycylglycine
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.
| Names | |
|---|---|
| IUPAC name
Glycylglycine | |
| Systematic IUPAC name
(2-Aminoacetamido)acetic acid | |
Other names
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| Identifiers | |
3D model (JSmol) |
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| 3DMet | |
| Abbreviations | Gly-Gly |
| 1765223 | |
| ChEBI | |
| ChEMBL | |
| ChemSpider | |
| ECHA InfoCard | 100.008.299 |
| EC Number |
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| 82735 | |
| KEGG | |
| MeSH | Glycylglycine |
PubChem CID |
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| UNII | |
CompTox Dashboard (EPA) |
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SMILES
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| Properties | |
| C4H8N2O3 | |
| Molar mass | 132.119 g·mol−1 |
| Appearance | White crystals |
| 132 g L−1 (at 20 °C) | |
| log P | −2.291 |
| Acidity (pKa) | 3.133 |
| Basicity (pKb) | 10.864 |
| UV-vis (λmax) | 260 nm |
| Absorbance | 0.075 |
| Thermochemistry | |
Heat capacity (C) |
163.97 J K−1 mol−1 |
Std molar entropy (S⦵298) |
180.3 J K−1 mol−1 |
Std enthalpy of formation (ΔfH⦵298) |
−749.0–−746.4 kJ mol−1 |
Std enthalpy of combustion (ΔcH⦵298) |
−1.9710–−1.9684 MJ mol−1 |
| Hazards | |
| GHS labelling: | |
| Warning | |
| H319 | |
| P305+P351+P338 | |
| Related compounds | |
Related alkanoic acids |
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Related compounds |
N-Acetylglycinamide |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references | |
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.