Glycolaldehyde

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Glycolaldehyde
Glycolaldehyde
Names
IUPAC name
2-hydroxyacetaldehyde
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.004.987 Edit this at Wikidata
KEGG
  • InChI=1S/C2H4O2/c3-1-2-4/h1,4H,2H2 checkY
    Key: WGCNASOHLSPBMP-UHFFFAOYSA-N checkY
  • InChI=1/C2H4O2/c3-1-2-4/h1,4H,2H2
    Key: WGCNASOHLSPBMP-UHFFFAOYAH
  • O=CCO
Properties
C2H4O2
Molar mass 60.052 g/mol
Density 1.065 g/mL
Boiling point 131.3 °C (268.3 °F; 404.4 K)
Related compounds
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)

Glycolaldehyde (HOCH2-CH=O) is the smallest possible molecule that contains both an aldehyde group and a hydroxyl group. It is the only possible diose, a 2-carbon monosaccharide, although a diose is not strictly a saccharide. While not a true sugar, it is the simplest sugar-related molecule.[1]

Formation

Glycolaldehyde is an intermediate in the formose reaction. Glycolaldehyde forms from many precursors, including the amino acid glycine. It can form by action of ketolase on fructose 1,6-bisphosphate in an alternate glycolysis pathway. This compound is transferred by thiamine pyrophosphate during the pentose phosphate shunt.

In purine catabolism, xanthine is first converted to urate. This is converted to 5-hydroxyisourate, which decarboxylates to allantoin and allantoic acid. After hydrolyzing one urea, this leaves glycolureate. After hydrolyzing the second urea, glycolaldehyde is left. Two glycolaldehydes condense to form erythrose 4-phosphate, which goes to the pentose phosphate shunt again.

In space

Sugar molecules in the gas surrounding a young Sun-like star.[2]

Glycolaldehyde has been identified in gas and dust near the center of the Milky Way galaxy,[3] in a star-forming region 26000 light-years from Earth,[4] and around a protostellar binary star, IRAS 16293-2422, 400 light years from Earth.[5][6] Observation of in-falling glycolaldehyde spectra 60 AU from IRAS 16293-2422 suggests that complex organic molecules may form in stellar systems prior to the formation of planets, eventually arriving on young planets early in their formation.[7]

References

  1. ^ Carroll, P., Drouin, B., and Widicus Weaver, S., (2010). "The Submillimeter Spectrum of Glycolaldehyde" (PDF). Astrophys. J. 723: 845–849.{{cite journal}}: CS1 maint: extra punctuation (link) CS1 maint: multiple names: authors list (link)
  2. ^ "Sweet Result from ALMA". ESO Press Release. Retrieved 3 September 2012.
  3. ^ Hollis, J.M., Lovas, F.J., & Jewell, P.R. (2000). "Interstellar Glycolaldehyde: The First Sugar" (PDF). The Astrophysical Journal. 540 (2): 107–110. Bibcode:2000ApJ...540L.107H. doi:10.1086/312881.{{cite journal}}: CS1 maint: multiple names: authors list (link)
  4. ^ Beltran, M. T. (11/2008). "First detection of glycolaldehyde outside the Galactic Center". eprint arXiv:0811.3821. {{cite journal}}: Check date values in: |date= (help); Cite journal requires |journal= (help); Unknown parameter |coauthors= ignored (|author= suggested) (help)CS1 maint: extra punctuation (link)
  5. ^ Than, Ker (August 29, 2012). "Sugar Found In Space". National Geographic. Retrieved August 31, 2012.
  6. ^ Staff (August 29, 2012). "Sweet! Astronomers spot sugar molecule near star". AP News. Retrieved August 31, 2012.
  7. ^ Jørgensen, J. K. (2012). "Detection of the simplest sugar, glycolaldehyde, in a solar-type protostar with ALMA" (PDF). eprint. {{cite journal}}: Cite journal requires |journal= (help); Unknown parameter |coauthors= ignored (|author= suggested) (help)

External links

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