Glycylglycine

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
3D model (JSmol)
3DMet
Abbreviations Gly-Gly
1765223
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.008.299 Edit this at Wikidata
EC Number
  • 209-127-8
82735
KEGG
MeSH Glycylglycine
UNII
  • InChI=1S/C4H8N2O3/c5-1-3(7)6-2-4(8)9/h1-2,5H2,(H,6,7)(H,8,9) checkY
    Key: YMAWOPBAYDPSLA-UHFFFAOYSA-N checkY
  • NCC(=O)NCC(O)=O
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
163.97 J K−1 mol−1
180.3 J K−1 mol−1
−749.0–−746.4 kJ mol−1
−1.9710–−1.9684 MJ mol−1
Hazards
GHS labelling:
GHS07: Exclamation mark
Warning
H319
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 [77 °F], 100 kPa).
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Glycylglycine is the dipeptide of glycine, making it the simplest peptide.[1] The compound was first synthesized by Emil Fischer and Ernest Fourneau in 1901 by boiling 2,5-diketopiperazine (glycine anhydride) with hydrochloric acid.[2] Shaking with alkali[1] and other synthesis methods have been reported.[3]

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;[4] however, it is only moderately stable for storage once dissolved.[5] It is used in the synthesis of more complex peptides.[6]

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.[7]

References

  1. ^ a b 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) [1908]. 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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