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Glycylglycine

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Glycylglycine
Skeletal formula of glycylglycine
Names
IUPAC name Glycylglycine
Systematic IUPAC name (2-Aminoacetamido)acetic acid
Other names
  • Diglycine
  • Diglycocoll
  • Glycine dipeptide
  • Glycyl-glycine
  • N-Glycylglycine
Identifiers
CAS Number
3D model (JSmol)
3DMet
Abbreviations Gly-Gly
Beilstein Reference 1765223
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.008.299 Edit this at Wikidata
EC Number
  • 209-127-8
Gmelin Reference 82735
KEGG
MeSH Glycylglycine
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C4H8N2O3/c5-1-3(7)6-2-4(8)9/h1-2,5H2,(H,6,7)(H,8,9)Key: YMAWOPBAYDPSLA-UHFFFAOYSA-N
SMILES
  • NCC(=O)NCC(O)=O
Properties
Chemical formula C4H8N2O3
Molar mass 132.119 g·mol
Appearance White crystals
Solubility in water 132 g L (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 mol
Std molar
entropy (S298) 		180.3 J K mol
Std enthalpy of
formation (ΔfH298) 		−749.0–−746.4 kJ mol
Std enthalpy of
combustion (ΔcH298) 		−1.9710–−1.9684 MJ mol
Hazards
GHS labelling:
Pictograms GHS07: Exclamation mark
Signal word Warning
Hazard statements H319
Precautionary statements P305+P351+P338
Related compounds
Related alkanoic acids
Related compounds N-Acetylglycinamide
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). ☒N verify (what is  ?) Infobox references
Chemical compound

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.

References

  1. ^ von Richter, Victor (1916). R. Anschütz and G. Shroeter (ed.). Richter's organic chemistry. Vol. I. Chemistry of the aliphatic series. Translated and revised by Percy E. Spielman after Edgar F. Smith (3rd American ed.). Philadelphia: P. Blakiston's Son & Co. p. 391. Retrieved July 15, 2010.
  2. R.H.A. Plimmer (July 2008) . R.H.A. Plimmer & F.G. Hopkins (ed.). The chemical composition of the proteins. Monographs on biochemistry. Vol. Part II (1st ed.). London: Longmans, Green and Co. p. 22. ISBN 978-1-4097-9725-8. Retrieved July 15, 2010.
  3. Dunn, Max S.; A. W. Butler; T. Deakers (December 1, 1932). "The synthesis of glycylglycine" (PDF). Journal of Biological Chemistry. 99 (1). American Society for Biochemistry and Molecular Biology: 217–220. doi:10.1016/S0021-9258(18)76083-3. ISSN 0021-9258. Retrieved August 9, 2010.
  4. "Biological buffers". Sigma-Aldrich. 2010. Retrieved August 9, 2010.
  5. Smith, Marshall E.; Smith, Lynwood B. (June 1, 1949). "Piperazine dihydrochloride and glycylglycine as non-toxic buffers in distilled water and sea water" (PDF). The Biological Bulletin. 96 (3). Woods Hole, MA: Marine Biological Laboratory: 233–237. doi:10.2307/1538357. ISSN 0006-3185. JSTOR 1538357. PMID 18153110. Retrieved August 9, 2010.
  6. Budavari, Susan, ed. (1989). The Merck Manual (11th ed.). Rahway, NJ: Merck & Co. pp. 707–8. ISBN 0-911910-28-X.
  7. Ghosh, S; Rasheedi, S; Rahim, SS; Banerjee, S; Choudhary, RK; Chakhaiyar, P; Ehtesham, NZ; Mukhopadhyay, S; Hasnain, SE (2004). "Method for enhancing solubility of the expressed recombinant proteins in Escherichia coli". BioTechniques. 37 (3): 418, 420, 422–3. doi:10.2144/04373ST07. PMID 15470897.
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