10.1002/anie.201901059
Angewandte Chemie International Edition
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[13] D. Gerbig, P. R. Schreiner, J. Phys. Chem. B 2015, 119, 693-703.
[14] C. Menor-Salván, M. R. Marín-Yaseli, Chem. Eur. J. 2013, 19, 6488-
6497.
Therefore, the formation and detection of 1 in our laboratory
simulation experiments should trigger future astronomical
searches toward SgrB2(N-LMH) – a hot core in which various
organic molecules such as 4 have been observed – with the
Atacama Large Millimeter/sub-millimeter Array (ALMA).
[15] M. R. Marín-Yaseli, E. González-Toril, C. Mompeán, M. Ruiz-Bermejo,
Chem. Eur. J. 2016, 22, 12785-12799.
[16] F. S. Mohammed, K. Chen, M. Mojica, M. Conley, J. W. Napoline, C.
Butch, P. Pollet, R. Krishnamurthy, C. L. Liotta, Synlett 2017, 28, 93-97.
[17] a) C. J. Bennett, C. S. Jamieson, Y. Osamura, R. I. Kaiser, Astrophys. J.
2005, 624, 1097-1115; b) C. J. Bennett, Y. Osamura, M. D. Lebar, R. I.
Kaiser, Astrophys. J. 2005, 634, 698-711.
The exploitation of interstellar model ices represents
a
substantiated strategy and original step as validated by, e.g.,
Meinert and co-workers and Ehrenfreund and co-workers.[31]
Future work may investigate the role of distinct interstellar
irradiation fields (e.g., photons vs. GRCs) and mineral-catalyzed
formation on the yield of glyoxylic acid, thus eventually
deciphering the fundamental molecular processes that might
have contributed to the inventory of prebiotic, biorelevant
compounds from which life could have emerged.
[18] E. L. Gibb, D. C. B. Whittet, W. A. Schutte, A. C. A. Boogert, J. E. Chiar,
P. Ehrenfreund, P. A. Gerakines, J. V. Keane, A. G. G. M. Tielens, E. F.
v. Dishoeck, O. Kerkhof, Astrophys. J. 2000, 536, 347-356.
[19] E. Herbst, Annu. Rev. Phys. Chem. 1995, 46, 27-54.
[20] a) R. I. Kaiser, K. Roessler, Astrophys. J. 1998, 503, 959-975; b) A.
Bergantini, S. Góbi, M. J. Abplanalp, R. I. Kaiser, Astrophys. J. 2018, 852,
70; c) M. J. Abplanalp, S. Gozem, A. I. Krylov, C. N. Shingledecker, E.
Herbst, R. I. Kaiser, Proc. Natl. Acad. Sci. USA 2016, 113, 7727-7732.
[21] a) R. N. Clayton, T. K. Mayeda, Geochim. Cosmochim. Acta 1999, 63,
2089-2104; b) J. F. Kerridge, S. Chang, R. Shipp, Geochim. Cosmochim.
Acta 1987, 51, 2527-2540.
Acknowledgements
[22] a) G. E. Ewing, W. E. Thompson, G. C. Pimentel, J. Chem. Phys. 1960,
32, 927-932; b) D. E. Milligan, M. E. Jacox, J. Chem. Phys. 1964, 41,
3032-3036.
A.K.E. thanks the Fonds der Chemischen Industrie for a
scholarship. This work was supported by the Volkswagen
Foundation (“What is Life” grant 92 748). The Hawaii group
acknowledges support from the US National Science Foundation,
Division of Astronomical Sciences under grant AST-1800975. The
equipment was financed by the W. M. Keck Foundation.
[23] D. E. Milligan, M. E. Jacox, J. Chem. Phys. 1971, 54, 927-942.
[24] a) M. H. Moore, R. Khanna, B. Donn, J. Geophys. Res. Planets 1991, 96,
17541-17545; b) R. L. Hudson, M. H. Moore, Icarus 1999, 140, 451-461;
c) W. Naoki, K. Akira, Astrophys. J. 2002, 567, 651-655; d) N. Watanabe,
O. Mouri, A. Nagaoka, T. Chigai, A. Kouchi, V. Pirronello, Astrophys. J.
2007, 668, 1001-1011; e) C. J. Bennett, T. Hama, Y. S. Kim, M. Kawasaki,
R. I. Kaiser, Astrophys. J. 2011, 727, 27; f) A. Jiménez-Escobar, Y. J.
Chen, A. Ciaravella, C. H. Huang, G. Micela, C. Cecchi-Pestellini,
Astrophys. J. 2016, 820, 25.
Keywords: glyoxylate scenario • mass spectrometry •
non-equilibrium chemistry • photoionization • reactive
intermediates
[25] S. V. Ryazantsev, V. I. Feldman, L. Khriachtchev, J. Am. Chem. Soc.
2017, 139, 9551-9557.
[1]
a) A. Eschenmoser, Chem. Biodivers. 2007, 4, 554-573; b) A.
Eschenmoser, Tetrahedron 2007, 63, 12821-12843; c) G. Springsteen,
J. R. Yerabolu, J. Nelson, C. J. Rhea, R. Krishnamurthy, Nat. Commun.
2018, 9, 91.
[26] a) J. z. Yang, L. Zhao, J. h. Cai, F. Qi, Y. y. Li, Chin. J. Chem. Phys. 2013,
26, 245-251; b) N. Hansen, J. A. Miller, C. A. Taatjes, J. Wang, T. A.
Cool, M. E. Law, P. R. Westmoreland, Proc. Combust. Inst. 2007, 31,
1157-1164.
[2]
C. Butch, E. D. Cope, P. Pollet, L. Gelbaum, R. Krishnamurthy, C. L.
Liotta, J. Am. Chem. Soc. 2013, 135, 13440-13445.
[27] a) A. Bergantini, P. Maksyutenko, R. I. Kaiser, Astrophys. J. 2017, 841,
96; b) W. Zheng, D. Jewitt, R. I. Kaiser, Astrophys. J. 2006, 639, 534-
548.
[3]
[4]
M. J. Plater, K. Vassiliev, J. Chem. Res. 2011, 35, 129-132.
a) A. Butlerow, Justus Liebigs Ann. Chem. 1861, 120, 295-298; b) R.
Breslow, Tetrahedron Lett. 1959, 1, 22-26.
[28] W. Zheng, Y. S. Kim, R. I. Kaiser, Phys. Chem. Chem. Phys. 2011, 13,
15749-15754.
[5]
a) D. J. Ritson, J. D. Sutherland, Angew. Chem. 2013, 125, 5957-5959;
Angew. Chem. Int. Ed. 2013, 52, 5845-5847; b) D. Ritson, J. D.
Sutherland, Nature Chem. 2012, 4, 895-899.
[29] M. H. Engel, S. A. Macko, Nature 1997, 389, 265-268.
[30] W. Martin, J. Baross, D. Kelley, M. J. Russell, Nat. Rev. Microbiol. 2008,
6, 805-814.
[6]
[7]
[8]
[9]
V. Naidu Sagi, P. Karri, F. Hu, R. Krishnamurthy, Angew. Chem. 2011,
123, 8277-8280; Angew. Chem. Int. Ed. 2011, 50, 8127-8130.
V. N. Sagi, V. Punna, F. Hu, G. Meher, R. Krishnamurthy, J. Am. Chem.
Soc. 2012, 134, 3577-3589.
[31] a) C. Meinert, J.-J. Filippi, P. de Marcellus, L. Le Sergeant d'Hendecourt,
U. J. Meierhenrich, ChemPlusChem 2012, 77, 186-191; b) C. Meinert, I.
Myrgorodska, P. de Marcellus, T. Buhse, L. Nahon, S. V. Hoffmann, L. L.
d'Hendecourt, U. J. Meierhenrich, Science 2016, 352, 208-212; c) P.
Modica, C. Meinert, P. d. Marcellus, L. Nahon, U. J. Meierhenrich, L. L.
S. d'Hendecourt, Astrophys. J. 2014, 788, 79; d) P. de Marcellus, C.
Meinert, I. Myrgorodska, L. Nahon, T. Buhse, S. d'Hendecourt Lle, U. J.
Meierhenrich, Proc. Natl. Acad. Sci. USA 2015, 112, 965-970; e) P.
Ehrenfreund, A. Boogert, P. Gerakines, A. Tielens, E. Van Dishoeck,
Astron. Astrophys. 1997, 328, 649-669; f) P. Ehrenfreund, Science 1999,
283, 1123-1124; g) P. Ehrenfreund, S. B. Charnley, Annu. Rev. Astron.
Astrophys. 2000, 38, 427-483.
a) R. W. Hay, S. J. Harvie, Aust. J. Chem. 1965, 18, 1197-1209; b) D. L.
Rohlfing, Arch. Biochem. Biophys. 1967, 118, 468-474.
P. R. Schreiner, H. P. Reisenauer, F. C. Pickard IV, A. C. Simmonett, W.
D. Allen, E. Matyus, A. G. Csaszar, Nature 2008, 453, 906-909.
[10] P. R. Schreiner, J. Am. Chem. Soc. 2017, 139, 15276-15283.
[11] a) G. Flanagan, S. N. Ahmed, P. B. Shevlin, J. Am. Chem. Soc. 1992,
114, 3892-3896; b) A. K. Eckhardt, M. M. Linden, R. C. Wende, B.
Bernhardt, P. R. Schreiner, Nature Chem. 2018, 10, 1141-1147.
[12] A. K. Eckhardt, R. C. Wende, P. R. Schreiner, J. Am. Chem. Soc. 2018,
140, 12333-12336.
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