Glycylglycine

Glycylglycine
Names
	IUPAC name 2-[(2-Aminoacetyl)amino]acetic acid
	Other names Diglycine; Diglycocoll; Glycine dipeptide; N-Glycylglycine;
Identifiers
CAS Number	556-50-3 ;
3D model (JSmol)	Interactive image;
3DMet	B00385;
Abbreviations	Gly-Gly
Beilstein Reference	1765223
ChEBI	CHEBI:17201 ;
ChEMBL	ChEMBL292467 ;
ChemSpider	10690 ;
ECHA InfoCard	100.008.299
EC Number	209-127-8;
Gmelin Reference	82735
KEGG	C02037 ;
MeSH	Glycylglycine
PubChem CID	11163;
UNII	10525P22U0 ;
CompTox Dashboard (EPA)	DTXSID90862194 ;
	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−1
Appearance	White crystals
Solubility in water	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:
Pictograms
Signal word	Warning
Hazard statements	H319
Precautionary statements	P305+P351+P338
Related compounds
Related alkanoic acids	Acetylcysteine; Iminodiacetic acid; Nitrilotriacetic acid; N-Oxalylglycine; Tiopronin; Bucillamine; Oxalyldiaminopropionic acid;
Related compounds	N-Acetylglycinamide
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

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

^ ^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.
^ 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.
^ 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. ISSN 0021-9258. Retrieved August 9, 2010.
^ "Biological buffers". Sigma-Aldrich. 2010. Retrieved August 9, 2010.
^ 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.
^ Budavari, Susan, ed. (1989). The Merck Manual (11th ed.). Rahway, NJ: Merck & Co. pp. 707–8. ISBN 0-911910-28-X.
^ 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. PMID 15470897.

[richter-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) [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. 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. PMID 15470897.

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