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Glycylglycine: Difference between revisions

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Revision as of 10:22, 9 August 2011 editBeetstra (talk | contribs)Edit filter managers, Administrators172,055 edits Script assisted update of identifiers for the Chem/Drugbox validation project (updated: 'ChEBI').← Previous edit Revision as of 10:33, 9 August 2011 edit undoCheMoBot (talk | contribs)Bots141,565 edits Updating {{chembox}} (no changed fields - added verified revid - updated 'DrugBank_Ref', 'ChEBI_Ref') per Chem/Drugbox validation (report errors or [[userNext edit →
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{{Chembox {{Chembox
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| CASNo = 556-50-3 | CASNo = 556-50-3
| PubChem = 11163 | PubChem = 11163
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 356445 | ChEBI = 356445
| SMILES = O=C(NCC(=O)O)CN | SMILES = O=C(NCC(=O)O)CN
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Revision as of 10:33, 9 August 2011

Glycylglycine
Names
IUPAC name 2-acetic acid
Other names N-Glycylglycine, Diglycine, Diglycocoll, Glycine dipeptide
Identifiers
CAS Number
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.008.299 Edit this at Wikidata
KEGG
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
  • InChI=1/C4H8N2O3/c5-1-3(7)6-2-4(8)9/h1-2,5H2,(H,6,7)(H,8,9)Key: YMAWOPBAYDPSLA-UHFFFAOYAO
SMILES
  • O=C(NCC(=O)O)CN
Properties
Chemical formula C4H8N2O3
Molar mass 132.11792
Melting point 262-264°C (decomposes)
Solubility in water 229.9 g/kg (25 °C)
Acidity (pKa) 3.12, 8.17
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). checkY 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.


References

  1. ^ Budavari, Susan, ed. (1989). The Merck Manual (11th ed.). Rahway, NJ: Merck & Co. pp. 707–8. ISBN 91191028X. {{cite book}}: Check |isbn= value: length (help)
  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. ^ 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.
  4. R.H.A. Plimmer (2008-07) . 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 9781409797258. Retrieved July 15, 2010. {{cite book}}: Check date values in: |date= (help)
  5. Dunn, Max S. (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. {{cite journal}}: Unknown parameter |coauthors= ignored (|author= suggested) (help)
  6. "Biological buffers". Sigma-Aldrich. 2010. Retrieved August 9, 2010.
  7. Smith, Marshall E. (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. {{cite journal}}: Unknown parameter |coauthors= ignored (|author= suggested) (help)
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