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Glycolaldehyde

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Glycolaldehyde
Glycolaldehyde
Names
Preferred IUPAC name
Hydroxyacetaldehyde
Systematic IUPAC name
Hydroxyethanal
Other names
2-Hydroxyacetaldehyde
2-Hydroxyethanal
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.004.987 Edit this at Wikidata
KEGG
UNII
  • 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
Melting point 97 °C (207 °F; 370 K)
Boiling point 131.3 °C (268.3 °F; 404.4 K)
Related compounds
Related aldehydes
 3-Hydroxybutanal

Lactaldehyde

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 is the organic compound with the formula HOCH2−CHO. It is the smallest possible molecule that contains both an aldehyde group (−CH=O) and a hydroxyl group (−OH). It is a highly reactive molecule that occurs both in the biosphere and in the interstellar medium. It is normally supplied as a white solid. Although it conforms to the general formula for carbohydrates, Cn(H2O)n, it is not generally considered to be a saccharide.[1]

Structure

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Glycolaldehyde as a gas is a simple monomeric structure. As a solid and molten liquid, it exists as a dimer. Collins and George reported the equilibrium of glycolaldehyde in water by using NMR.[2][3] In aqueous solution, it exists as a mixture of at least four species, which rapidly interconvert.[4]

Structures and distribution of glycolaldehyde as a 20% solution in water. Notice that the free aldehyde is a minor component.

In acidic or basic solution, the compound undergoes reversible tautomerization to form 1,2-dihydroxyethene.[5]

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.[6] It is reported to taste sweet.[7]

Synthesis

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Glycolaldehyde is the second most abundant compound formed when preparing pyrolysis oil (up to 10% by weight).[8]

Glycolaldehyde can be synthesized by the oxidation of ethylene glycol using hydrogen peroxide in the presence of iron(II) sulfate.[9]

Biosynthesis

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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,[citation needed] which goes to the pentose phosphate shunt again.

Role in formose reaction

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Glycolaldehyde is an intermediate in the formose reaction. In the formose reaction, two formaldehyde molecules condense to make glycolaldehyde. Glycolaldehyde then is converted to glyceraldehyde, presumably via initial tautomerization.[10] The presence of this glycolaldehyde in this reaction demonstrates how it might play an important role in the formation of the chemical building blocks of life. Nucleotides, for example, rely on the formose reaction to attain its sugar unit. Nucleotides are essential for life, because they compose the genetic information and coding for life.

Theorized role in abiogenesis

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It is often invoked in theories of abiogenesis.[11][12] In the laboratory, amino acids[13] and short dipeptides[14] have been shown to catalyze the formation of complex sugars from glycolaldehyde. For example, L-valyl-L-valine was used as a catalyst to form tetroses from glycolaldehyde. Theoretical calculations have additionally shown the feasibility of dipeptide-catalyzed synthesis of pentoses.[15] This formation showed stereospecific, catalytic synthesis of D-ribose, the only naturally occurring enantiomer of ribose. Since the detection of this organic compound, many theories have been developed related various chemical routes to explain its formation in stellar systems.

Formation of glycolaldehyde in star dust

It was found that UV-irradiation of methanol ices containing CO yielded organic compounds such as glycolaldehyde and methyl formate, the more abundant isomer of glycolaldehyde. The abundances of the products slightly disagree with the observed values found in IRAS 16293-2422, but this can be accounted for by temperature changes. Ethylene Glycol and glycolaldehyde require temperatures above 30 K.[16][17] The general consensus among the astrochemistry research community is in favor of the grain surface reaction hypothesis. However, some scientists believe the reaction occurs within denser and colder parts of the core. The dense core will not allow for irradiation as stated before. This change will completely alter the reaction forming glycolaldehyde.[18]

Formation in space

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Main article: List of interstellar and circumstellar molecules
Artistic depiction of sugar molecules in the gas surrounding a young Sun-like star.[19]

The different conditions studied indicate how problematic it could be to study chemical systems that are light-years away. The conditions for the formation of glycolaldehyde are still unclear. At this time, the most consistent formation reactions seems to be on the surface of ice in cosmic dust.

Glycolaldehyde has been identified in gas and dust near the center of the Milky Way galaxy,[20] in a star-forming region 26000 light-years from Earth,[21] and around a protostellar binary star, IRAS 16293-2422, 400 light years from Earth.[22][23] 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.[17]

Detection in space

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The interior region of a dust cloud is known to be relatively cold. With temperatures as cold as 4 Kelvin, the gases within the cloud will freeze and fasten themselves to the dust, which provides the reaction conditions conducive for the formation of complex molecules such as glycolaldehyde. When a star has formed from the dust cloud, the temperature within the core will increase. This will cause the molecules on the dust to evaporate and be released. The molecule will emit radio waves that can be detected and analyzed. The Atacama Large Millimeter/submillimeter Array (ALMA) first detected glycolaldehyde. ALMA consists of 66 antennas that can detect the radio waves emitted from cosmic dust.[24]

On October 23, 2015, researchers at the Paris Observatory announced the discovery of glycolaldehyde and ethyl alcohol on Comet Lovejoy, the first such identification of these substances in a comet.[25][26]

References

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  1. ^ Mathews, Christopher K. (2000). Biochemistry. Van Holde, K. E. (Kensal Edward), 1928-, Ahern, Kevin G. (3rd ed.). San Francisco, Calif.: Benjamin Cummings. p. 280. ISBN 978-0805330663. OCLC 42290721.
  2. ^ "Prediction of Isomerization of Glycolaldehyde In Aqueous Solution by IBM RXN – Artificial Intelligence for Chemistry". 11 November 2019. Retrieved 2019-11-19.
  3. ^ Collins, G. C. S.; George, W. O. (1971). "Nuclear magnetic resonance spectra of glycolaldehyde". Journal of the Chemical Society B: Physical Organic: 1352. doi:10.1039/j29710001352. ISSN 0045-6470.
  4. ^ Yaylayan, Varoujan A.; Harty-Majors, Susan; Ismail, Ashraf A. (1998). "Investigation of the mechanism of dissociation of glycolaldehyde dimer (2,5-dihydroxy-1,4-dioxane) by FTIR spectroscopy". Carbohydrate Research. 309: 31–38. doi:10.1016/S0008-6215(98)00129-3.
  5. ^ Fedoroňko, Michal; Temkovic, Peter; Königstein, Josef; Kováčik, Vladimir; Tvaroška, Igor (1 December 1980). "Study of the kinetics and mechanism of the acid-base-catalyzed enolization of hydroxyacetaldehyde and methoxyacetaldehyde". Carbohydrate Research. 87 (1): 35–50. doi:10.1016/S0008-6215(00)85189-7.
  6. ^ Carroll, P.; Drouin, B.; Widicus Weaver, S. (2010). "The Submillimeter Spectrum of Glycolaldehyde" (PDF). Astrophys. J. 723 (1): 845–849. Bibcode:2010ApJ...723..845C. doi:10.1088/0004-637X/723/1/845. S2CID 30104627.
  7. ^ Shallenberger, R. S. (2012-12-06). Taste Chemistry. Springer Science & Business Media. ISBN 9781461526667.
  8. ^ Moha, Dinesh; Charles U. Pittman, Jr.; Philip H. Steele (10 March 2006). "Pyrolysis of Wood/Biomass for Bio-oil: A Critical Review". Energy & Fuels. 206 (3): 848–889. doi:10.1021/ef0502397. S2CID 49239384.
  9. ^ {{Hans Peter Latscha, Uli Kazmaier und Helmut Alfons Klein : Organic Chemistry: Chemistry Basiswissen-II '. Springer, Berlin; 6, vollständig überarbeitete Auflage 2008, ISBN 978-3-540-77106-7, S. 217}}
  10. ^ Kleimeier, N. Fabian; Eckhardt, André K.; Kaiser, Ralf I. (August 18, 2021). "Identification of Glycolaldehyde Enol (HOHC═CHOH) in Interstellar Analogue Ices". J. Am. Chem. Soc. 143 (34): 14009–14018. doi:10.1021/jacs.1c07978. PMID 34407613. S2CID 237215450.
  11. ^ Kim, H.; Ricardo, A.; Illangkoon, H. I.; Kim, M. J.; Carrigan, M. A.; Frye, F.; Benner, S. A. (2011). "Synthesis of Carbohydrates in Mineral-Guided Prebiotic Cycles". Journal of the American Chemical Society. 133 (24)): 9457–9468. doi:10.1021/ja201769f. PMID 21553892.
  12. ^ Benner, S. A.; Kim, H.; Carrigan, M. A. (2012). "Asphalt, Water, and the Prebiotic Synthesis of Ribose, Ribonucleosides, and RNA". Accounts of Chemical Research. 45 (12): 2025–2034. doi:10.1021/ar200332w. PMID 22455515. S2CID 10581856.
  13. ^ Pizzarello, Sandra; Weber, A. L. (2004). "Prebiotic amino acids as asymmetric catalysts". Science. 303 (5661): 1151. CiteSeerX 10.1.1.1028.833. doi:10.1126/science.1093057. PMID 14976304. S2CID 42199392.
  14. ^ Weber, Arthur L.; Pizzarello, S. (2006). "The peptide-catalyzed stereospecific synthesis of tetroses: A possible model for prebiotic molecular evolution". Proceedings of the National Academy of Sciences of the USA. 103 (34): 12713–12717. Bibcode:2006PNAS..10312713W. doi:10.1073/pnas.0602320103. PMC 1568914. PMID 16905650.
  15. ^ Cantillo, D.; Ávalos, M.; Babiano, R.; Cintas, P.; Jiménez, J. L.; Palacios, J. C. (2012). "On the Prebiotic Synthesis of D-Sugars Catalyzed by L-Peptides Assessments from First-Principles Calculations". Chemistry: A European Journal. 18 (28): 8795–8799. doi:10.1002/chem.201200466. PMID 22689139.
  16. ^ Öberg, K. I.; Garrod, R. T.; van Dishoeck, E. F.; Linnartz, H. (September 2009). "Formation rates of complex organics in UV irradiation CH_3OH-rich ices. I. Experiemtns". Astronomy and Astrophysics. 504 (3): 891–913. arXiv:0908.1169. Bibcode:2009A&A...504..891O. doi:10.1051/0004-6361/200912559. S2CID 7746611.
  17. ^ a b Jørgensen, J. K.; Favre, C.; Bisschop, S.; Bourke, T.; Dishoeck, E.; Schmalzl, M. (2012). "Detection of the simplest sugar, glycolaldehyde, in a solar-type protostar with ALMA" (PDF). The Astrophysical Journal. eprint. 757 (1): L4. arXiv:1208.5498. Bibcode:2012ApJ...757L...4J. doi:10.1088/2041-8205/757/1/L4. S2CID 14205612.
  18. ^ Woods, P. M; Kelly, G.; Viti, S.; Slater, B.; Brown, W. A.; Puletti, F.; Burke, D. J.; Raza, Z. (2013). "Glycolaldehyde Formation via the Dimerisation of the Formyl Radical". The Astrophysical Journal. 777 (50): 90. arXiv:1309.1164. Bibcode:2013ApJ...777...90W. doi:10.1088/0004-637X/777/2/90. S2CID 13969635.
  19. ^ "Sweet Result from ALMA". ESO Press Release. Retrieved 3 September 2012.
  20. ^ Hollis, J.M., Lovas, F.J., & Jewell, P.R. (2000). "Interstellar Glycolaldehyde: The First Sugar". The Astrophysical Journal. 540 (2): 107–110. Bibcode:2000ApJ...540L.107H. doi:10.1086/312881.{{cite journal}}: CS1 maint: multiple names: authors list (link)
  21. ^ Beltran, M. T.; Codella, C.; Viti, S.; Neri, R.; Cesaroni, R. (November 2008). "First detection of glycolaldehyde outside the Galactic Center". eprint arXiv:0811.3821. {{cite journal}}: Cite journal requires |journal= (help)[permanent dead link]
  22. ^ Than, Ker (August 29, 2012). "Sugar Found In Space". National Geographic. Archived from the original on September 1, 2012. Retrieved August 31, 2012.
  23. ^ Staff (August 29, 2012). "Sweet! Astronomers spot sugar molecule near star". AP News. Retrieved August 31, 2012.
  24. ^ "Building blocks of life found around young star". Retrieved December 11, 2013.
  25. ^ Biver, Nicolas; Bockelée-Morvan, Dominique; Moreno, Raphaël; Crovisier, Jacques; Colom, Pierre; Lis, Dariusz C.; Sandqvist, Aage; Boissier, Jérémie; Despois, Didier; Milam, Stefanie N. (2015). "Ethyl alcohol and sugar in comet C/2014 Q2 (Lovejoy)". Science Advances. 1 (9): e1500863. arXiv:1511.04999. Bibcode:2015SciA....1E0863B. doi:10.1126/sciadv.1500863. PMC 4646833. PMID 26601319.
  26. ^ "Researchers find ethyl alcohol and sugar in a comet ! -".
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