Glycylglycine

Glycylglycine
IUPAC name

2-[(2-aminoacetyl)amino]acetic acid
Other names

N-Glycylglycine, Diglycine, Diglycocoll, Glycine dipeptide
Identifiers
CAS number 556-50-3 Y
PubChem 11163
ChemSpider 10690 Y
UNII 10525P22U0 Y
KEGG C02037 Y
ChEBI CHEBI:356445 Y
ChEMBL CHEMBL292467 Y
Jmol-3D images Image 1
Properties
Molecular formula C4H8N2O3
Molar mass 132.12 g mol−1
Melting point

262-264°C (decomposes)[1]
Solubility in water 229.9 g/kg (25 °C) [2]
Acidity (pKa) 3.12, 8.17 [1]
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Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Glycylglycine is the dipeptide of glycine, making it the simplest peptide.[3] The compound was first synthesized by Emil Fischer and Ernest Fourneau in 1901 by boiling 2,5-diketopiperazine (glycine anhydride) with hydrochloric acid.[4] Shaking with alkali[3] and other synthesis methods have been reported.[5]

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,[6] however, it is only moderately stable for storage once dissolved.[7] It is used in the synthesis of more complex peptides.[1]

References

  1. ^ a b c Budavari, Susan, ed (1989). The Merck Manual (11th ed.). Rahway, NJ: Merck & Co.. pp. 707–8. ISBN 91191028X. 
  2. ^ http://www.sciencedirect.com/science?_ob=ArticleURL&_udi=B6TG2-49S7YRF-2&_user=10&_coverDate=02%2F01%2F2004&_rdoc=1&_fmt=high&_orig=gateway&_origin=gateway&_sort=d&_docanchor=&view=c&_searchStrId=1752347990&_rerunOrigin=google&_acct=C000050221&_version=1&_urlVersion=0&_userid=10&md5=98c35dd19acf19f30e3c742f1f919a62&searchtype=a
  3. ^ a b von Richter, Victor (1916). R. Anschütz and G. Shroeter. ed. Richter's organic chemistry. 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. http://books.google.com/books?id=1mMFAQAAIAAJ&pg=PA391. Retrieved July 15, 2010. 
  4. ^ R.H.A. Plimmer (2008-07) [1908]. R.H.A. Plimmer & F.G. Hopkins. ed. The chemical composition of the proteins. Monographs on biochemistry. Part II (1st ed.). London: Longmans, Green and Co.. p. 22. ISBN 9781409797258. http://books.google.com/books?id=_eRVISVkC7AC. Retrieved July 15, 2010. 
  5. ^ Dunn, Max S.; A. W. Butler, T. Deakers (December 1, 1932). "The synthesis of glycylglycine" (PDF). Journal of Biological Chemistry (American Society for Biochemistry and Molecular Biology) 99 (1): 217–220. ISSN 0021-9258. http://www.jbc.org/content/99/1/217.full.pdf. Retrieved August 9, 2010. 
  6. ^ "Biological buffers". Sigma-Aldrich. 2010. http://www.sigmaaldrich.com/life-science/metabolomics/bioultra-reagents/biological-buffers.html. Retrieved August 9, 2010. 
  7. ^ Smith, Marshall E.; Smith, Lynwood B. (June 1, 1949). "Piperazine dihydrochloride and glycylglycine as non-toxic buffers in distilled water and sea water". The Biological Bulletin (Woods Hole, MA: Marine Biological Laboratory) 96 (3): 233–237. doi:10.2307/1538357. ISSN 0006-3185. JSTOR 1538357. PMID 18153110. http://www.biolbull.org/cgi/reprint/96/3/233.pdf. Retrieved August 9, 2010.