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Glycolaldehyde

December 04, 2023

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]

Glycolaldehyde
Names
Preferred IUPAC name
Hydroxyacetaldehyde
Systematic IUPAC name
Hydroxyethanal
Other names
2-Hydroxyacetaldehyde
2-Hydroxyethanal
Identifiers
  • 141-46-8 Y
3D model (JSmol)
  • Interactive image
ChEBI
  • CHEBI:17071 Y
ChemSpider
  • 736 Y
ECHA InfoCard 100.004.987
KEGG
  • C00266 Y
  • 756
UNII
  • W0A0XPU08U Y
  • DTXSID4074693
  • InChI=1S/C2H4O2/c3-1-2-4/h1,4H,2H2 Y
    Key: WGCNASOHLSPBMP-UHFFFAOYSA-N Y
  • 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).
Y verify (what is YN ?)

Structure edit

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 edit

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 edit

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 edit

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 edit

It is often invoked in theories of abiogenesis.[11][12] In the laboratory, it can be converted to amino acids[13] and short dipeptides[14] may have facilitated the formation of complex sugars. 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 edit

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 edit

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 edit

  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.{{cite journal}}: CS1 maint: date and year (link)
  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). . 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 ! -".

External links edit

  • "Cold Sugar in Space Provides Clue to the Molecular Origin of Life". National Radio Astronomy Observatory. September 20, 2004. Retrieved December 20, 2006.

December 04, 2023
glycolaldehyde, organic, compound, with, formula, hoch2, smallest, possible, molecule, that, contains, both, aldehyde, group, hydroxyl, group, highly, reactive, molecule, that, occurs, both, biosphere, interstellar, medium, normally, supplied, white, solid, al. 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 Glycolaldehyde NamesPreferred IUPAC name HydroxyacetaldehydeSystematic IUPAC name HydroxyethanalOther names 2 Hydroxyacetaldehyde2 HydroxyethanalIdentifiersCAS Number 141 46 8 Y3D model JSmol Interactive imageChEBI CHEBI 17071 YChemSpider 736 YECHA InfoCard 100 004 987KEGG C00266 YPubChem CID 756UNII W0A0XPU08U YCompTox Dashboard EPA DTXSID4074693InChI InChI 1S C2H4O2 c3 1 2 4 h1 4H 2H2 YKey WGCNASOHLSPBMP UHFFFAOYSA N YInChI 1 C2H4O2 c3 1 2 4 h1 4H 2H2Key WGCNASOHLSPBMP UHFFFAOYAHSMILES O CCOPropertiesChemical formula C2H4O2Molar mass 60 052 g molDensity 1 065 g mLMelting point 97 C 207 F 370 K Boiling point 131 3 C 268 3 F 404 4 K Related compoundsRelated aldehydes 3 HydroxybutanalLactaldehydeExcept where otherwise noted data are given for materials in their standard state at 25 C 77 F 100 kPa Y verify what is Y N Infobox references Contents 1 Structure 2 Synthesis 2 1 Biosynthesis 2 2 Role in formose reaction 2 3 Theorized role in abiogenesis 3 Formation in space 3 1 Detection in space 4 References 5 External linksStructure editGlycolaldehyde 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 nbsp 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 editGlycolaldehyde 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 edit 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 edit 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 edit It is often invoked in theories of abiogenesis 11 12 In the laboratory it can be converted to amino acids 13 and short dipeptides 14 may have facilitated the formation of complex sugars 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 nbsp Formation of glycolaldehyde in star dustIt 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 editMain article List of interstellar and circumstellar molecules nbsp 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 edit 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 edit 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 Prediction of Isomerization of Glycolaldehyde In Aqueous Solution by IBM RXN Artificial Intelligence for Chemistry 11 November 2019 Retrieved 2019 11 19 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 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 Fedoronko Michal Temkovic Peter Konigstein Josef Kovacik Vladimir Tvaroska 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 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 Shallenberger R S 2012 12 06 Taste Chemistry Springer Science amp Business Media ISBN 9781461526667 Moha Dinesh Charles U Pittman Jr Philip H Steele 10 March 2006 Pyrolysis of Wood Biomass for Bio oil A Critical Review Energy amp Fuels 206 3 848 889 doi 10 1021 ef0502397 S2CID 49239384 Hans Peter Latscha Uli Kazmaier und Helmut Alfons Klein Organic Chemistry Chemistry Basiswissen II Springer Berlin 6 vollstandig uberarbeitete Auflage 2008 ISBN 978 3 540 77106 7 S 217 Kleimeier N Fabian Eckhardt Andre 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 a href Template Cite journal html title Template Cite journal cite journal a CS1 maint date and year link 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 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 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 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 Cantillo D Avalos M Babiano R Cintas P Jimenez 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 Oberg 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 amp A 504 891O doi 10 1051 0004 6361 200912559 S2CID 7746611 a b Jorgensen 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 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 Sweet Result from ALMA ESO Press Release Retrieved 3 September 2012 Hollis J M Lovas F J amp Jewell P R 2000 Interstellar Glycolaldehyde The First Sugar The Astrophysical Journal 540 2 107 110 Bibcode 2000ApJ 540L 107H doi 10 1086 312881 a href Template Cite journal html title Template Cite journal cite journal a CS1 maint multiple names authors list link 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 a href Template Cite journal html title Template Cite journal cite journal a Cite journal requires journal help permanent dead link Than Ker August 29 2012 Sugar Found In Space National Geographic Archived from the original on September 1 2012 Retrieved August 31 2012 Staff August 29 2012 Sweet Astronomers spot sugar molecule near star AP News Retrieved August 31 2012 Building blocks of life found around young star Retrieved December 11 2013 Biver Nicolas Bockelee Morvan Dominique Moreno Raphael Crovisier Jacques Colom Pierre Lis Dariusz C Sandqvist Aage Boissier Jeremie 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 Researchers find ethyl alcohol and sugar in a comet External links edit Cold Sugar in Space Provides Clue to the Molecular Origin of Life National Radio Astronomy Observatory September 20 2004 Retrieved December 20 2006 Portals nbsp Astronomy nbsp Biology Retrieved from https en wikipedia org w index php title Glycolaldehyde amp oldid 1186569344, wikipedia, wiki, book, books, library,

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