Gas-phase synthesis of racemic helicenes and their potential role in the enantiomeric enrichment of sugars and amino acids in meteorites

Kaiser, Ralf I.; Zhao, Long; Lu, Wenchao; Ahmed, Musahid; Evseev, Mikhail M.; Azyazov, Valeriy N.; Mebel, Alexander M.; Mohamed, Rana K.; Fischer, Felix R.; Li, Xiaohu

doi:10.1039/d2cp03084e

Title: Gas-phase synthesis of racemic helicenes and their potential role in the enantiomeric enrichment of sugars and amino acids in meteorites

Journal Article · Sat Sep 03 00:00:00 EDT 2022 · Physical Chemistry Chemical Physics. PCCP

DOI:https://doi.org/10.1039/d2cp03084e· OSTI ID:2325993

^[1]; Zhao, Long ^[1];

^[2];

^[2]; Evseev, Mikhail M. ^[3]; Azyazov, Valeriy N. ^[3];

^[4]; Mohamed, Rana K. ^[5]; Fischer, Felix R. ^[5];

^[6]

University of Hawaii at Manoa, Honolulu, HI (United States)
Lawrence Berkeley National Laboratory (LBNL), Berkeley, CA (United States)
Lebedev Physical Institute, Samara (Russia)
Florida International University (FIU), Miami, FL (United States)
University of California, Berkeley, CA (United States). Applied Science and Technology; Lawrence Berkeley National Laboratory (LBNL), Berkeley, CA (United States); Kavli Energy NanoScience Institute, Berkeley, CA (United States)
Chinese Academy of Sciences (CAS), Urumqi (China)

The molecular origins of homochirality on Earth is not understood well, particularly how enantiomerically enriched molecules of astrobiological significance like sugars and amino acids might have been synthesized on icy grains in space preceding their delivery to Earth. Polycyclic aromatic hydrocarbons (PAHs) identified in carbonaceous chondrites could have been processed in molecular clouds by circularly polarized light prior to the depletion of enantiomerically enriched helicenes onto carbonaceous grains resulting in chiral islands. However, the fundamental low temperature reaction mechanisms leading to racemic helicenes are still unknown. Here, by exploiting synchrotron based molecular beam photoionization mass spectrometry combined with electronic structure calculations, we provide compelling testimony on barrierless, low temperature pathways leading to racemates of [5] and [6]helicene. Astrochemical modeling advocates that gas-phase reactions in molecular clouds lead to racemates of helicenes suggesting a pathway for future astronomical observation and providing a fundamental understanding for the origin of homochirality on early Earth.

View Accepted Manuscript (DOE)

Cite

Export

Save

Research Organization:: Lawrence Berkeley National Laboratory (LBNL), Berkeley, CA (United States)

Sponsoring Organization:: USDOE Office of Science (SC), Basic Energy Sciences (BES). Chemical Sciences, Geosciences & Biosciences Division (CSGB); Russian Federation; National Energy Research Scientific Computing Center (NERSC); USDOE

Grant/Contract Number:: AC02-05CH11231; FG02-03ER15411; FG02-04ER15570; 075-15-2021-597

OSTI ID:: 2325993

Alternate ID(s):: OSTI ID: 1885468

Journal Information:: Physical Chemistry Chemical Physics. PCCP, Vol. 24, Issue 41; ISSN 1463-9076

Publisher:: Royal Society of ChemistryCopyright Statement

Country of Publication:: United States

Language:: English

References (56)

Pyrene synthesis in circumstellar envelopes and its role in the formation of 2D nanostructures Zhao, Long; Kaiser, Ralf I.; Xu, Bo Nature Astronomy, Vol. 2, Issue 5 https://doi.org/10.1038/s41550-018-0399-y	journal	March 2018
A Combined Experimental and Theoretical Study on the Formation of the Amino Acid Glycine (NH ₂ CH ₂ COOH) and Its Isomer (CH ₃ NHCOOH) in Extraterrestrial Ices Holtom, Philip D.; Bennett, Chris J.; Osamura, Yoshihiro The Astrophysical Journal, Vol. 626, Issue 2 https://doi.org/10.1086/430106	journal	June 2005
d -Amino acids in molecular evolution in space – Absolute asymmetric photolysis and synthesis of amino acids by circularly polarized light Sugahara, Haruna; Meinert, Cornelia; Nahon, Laurent Biochimica et Biophysica Acta (BBA) - Proteins and Proteomics, Vol. 1866, Issue 7 https://doi.org/10.1016/j.bbapap.2018.01.004	journal	July 2018
The molecular universe Tielens, A. G. G. M. Reviews of Modern Physics, Vol. 85, Issue 3 https://doi.org/10.1103/RevModPhys.85.1021	journal	July 2013
Low-temperature formation of polycyclic aromatic hydrocarbons in Titan’s atmosphere Zhao, Long; Kaiser, Ralf I.; Xu, Bo Nature Astronomy, Vol. 2, Issue 12 https://doi.org/10.1038/s41550-018-0585-y	journal	October 2018
Beta decay and the origin of biological chirality: New experimental results House, J.; Rich, A.; Zitzewitz, P. W. Origins of Life, Vol. 14, Issue 1-4 https://doi.org/10.1007/BF00933685	journal	January 1984
Asymmetric photolysis of (RS)-leucine with circularly polarized ultraviolet light Flores, Jose J.; Bonner, William A.; Massey, Gail A. Journal of the American Chemical Society, Vol. 99, Issue 11 https://doi.org/10.1021/ja00453a018	journal	March 1977
Synthesis of a Helical Analogue of Kekulene: A Flexible π-Expanded Helicene with Large Helical Diameter Acting as a Soft Molecular Spring Nakakuki, Yusuke; Hirose, Takashi; Matsuda, Kenji Journal of the American Chemical Society, Vol. 140, Issue 45 https://doi.org/10.1021/jacs.8b09825	journal	October 2018
A Combined Experimental and Theoretical Study on the Formation of Interstellar Propylene Oxide (CH ₃ CHCH ₂ O)—A Chiral Molecule Bergantini, Alexandre; Abplanalp, Matthew J.; Pokhilko, Pavel The Astrophysical Journal, Vol. 860, Issue 2 https://doi.org/10.3847/1538-4357/aac383	journal	June 2018
Enantiomeric Excesses Induced in Amino Acids by Ultraviolet Circularly Polarized Light Irradiation of Extraterrestrial ice Analogs: a Possible Source of Asymmetry for Prebiotic Chemistry Modica, Paola; Meinert, Cornelia; de Marcellus, Pierre The Astrophysical Journal, Vol. 788, Issue 1 https://doi.org/10.1088/0004-637X/788/1/79	journal	May 2014
Stern–Gerlach-Type Separations of Structural and Chiral Isomers by Interstellar Magnets Stevenson, Cheryl D.; Davis, John P. ACS Earth and Space Chemistry, Vol. 4, Issue 12 https://doi.org/10.1021/acsearthspacechem.0c00242	journal	November 2020
Magnetars and Magnetic Separation of Chiral Radicals in Interstellar Space: Homochirality Stevenson, Cheryl D.; Davis, John P. The Journal of Physical Chemistry A, Vol. 123, Issue 44 https://doi.org/10.1021/acs.jpca.9b07817	journal	October 2019
Low temperature formation of naphthalene and its role in the synthesis of PAHs (Polycyclic Aromatic Hydrocarbons) in the interstellar medium Parker, D. S. N.; Zhang, F.; Kim, Y. S. Proceedings of the National Academy of Sciences, Vol. 109, Issue 1 https://doi.org/10.1073/pnas.1113827108	journal	December 2011
Detection of the aromatic molecule benzonitrile ( c -C ₆ H ₅ CN) in the interstellar medium McGuire, Brett A.; Burkhardt, Andrew M.; Kalenskii, Sergei Science, Vol. 359, Issue 6372 https://doi.org/10.1126/science.aao4890	journal	January 2018
On the Abundance Gradients of Organic Molecules along the TMC‐1 Ridge Markwick, A. J.; Millar, T. J.; Charnley, S. B. The Astrophysical Journal, Vol. 535, Issue 1 https://doi.org/10.1086/308814	journal	May 2000
Homochirality Originates from the Handedness of Helices Liu, Shubin The Journal of Physical Chemistry Letters, Vol. 11, Issue 20 https://doi.org/10.1021/acs.jpclett.0c02144	journal	September 2020
Ribose and related sugars from ultraviolet irradiation of interstellar ice analogs Meinert, C.; Myrgorodska, I.; de Marcellus, P. Science, Vol. 352, Issue 6282 https://doi.org/10.1126/science.aad8137	journal	April 2016
The UMIST database for astrochemistry 2012 McElroy, D.; Walsh, C.; Markwick, A. J. Astronomy & Astrophysics, Vol. 550 https://doi.org/10.1051/0004-6361/201220465	journal	January 2013
Strain-induced helical chirality in polyaromatic systems Rickhaus, Michel; Mayor, Marcel; Juríček, Michal Chemical Society Reviews, Vol. 45, Issue 6 https://doi.org/10.1039/C5CS00620A	journal	January 2016
Low-temperature Formation of Carbonaceous Dust Grains from PAHs Gavilan Marin, Lisseth; Bejaoui, Salma; Haggmark, Michael The Astrophysical Journal, Vol. 889, Issue 2 https://doi.org/10.3847/1538-4357/ab62b7	journal	January 2020
Assessing the origins of aliphatic amines in the Murchison meteorite from their compound-specific carbon isotopic ratios and enantiomeric composition Aponte, José C.; Dworkin, Jason P.; Elsila, Jamie E. Geochimica et Cosmochimica Acta, Vol. 141 https://doi.org/10.1016/j.gca.2014.06.035	journal	September 2014
Chirality in Chemistry Prelog, Vladimir Science, Vol. 193, Issue 4247 https://doi.org/10.1126/science.935852	journal	July 1976
A Spectroscopic View on Cosmic PAH Emission Peeters, Els; Mackie, Cameron; Candian, Alessandra Accounts of Chemical Research, Vol. 54, Issue 8 https://doi.org/10.1021/acs.accounts.0c00747	journal	March 2021
From Interstellar Amino Acids to Prebiotic Catalytic Peptides: A Review Brack, André Chemistry & Biodiversity, Vol. 4, Issue 4 https://doi.org/10.1002/cbdv.200790057	journal	April 2007
Asymmetric Autocatalysis of Pyrimidyl Alkanol and Its Application to the Study on the Origin of Homochirality Soai, Kenso; Kawasaki, Tsuneomi; Matsumoto, Arimasa Accounts of Chemical Research, Vol. 47, Issue 12 https://doi.org/10.1021/ar5003208	journal	November 2014
Low-temperature synthesis of polycyclic aromatic hydrocarbons in Titan’s surface ices and on airless bodies Abplanalp, Matthew J.; Frigge, Robert; Kaiser, Ralf I. Science Advances, Vol. 5, Issue 10 https://doi.org/10.1126/sciadv.aaw5841	journal	October 2019
Chiral Molecular Carbon Nanostructures Fernández-García, Jesús M.; Evans, Paul J.; Filippone, Salvatore Accounts of Chemical Research, Vol. 52, Issue 6 https://doi.org/10.1021/acs.accounts.9b00144	journal	May 2019
Enantiomer excesses of rare and common sugar derivatives in carbonaceous meteorites Cooper, George; Rios, Andro C. Proceedings of the National Academy of Sciences, Vol. 113, Issue 24 https://doi.org/10.1073/pnas.1603030113	journal	May 2016
Non-racemic amino acids in the Murray and Murchison meteorites Pizzarello, S.; Cronin, J. R. Geochimica et Cosmochimica Acta, Vol. 64, Issue 2 https://doi.org/10.1016/S0016-7037(99)00280-X	journal	January 2000
The Helicenes: Potential Carriers of Diffuse Interstellar Bands Oña-Ruales, Jorge O.; Ruiz-Morales, Yosadara; Alvarez-Ramírez, Fernando ACS Earth and Space Chemistry, Vol. 5, Issue 2 https://doi.org/10.1021/acsearthspacechem.0c00235	journal	January 2021
Formation of benzene in the interstellar medium Jones, B. M.; Zhang, F.; Kaiser, R. I. Proceedings of the National Academy of Sciences, Vol. 108, Issue 2 https://doi.org/10.1073/pnas.1012468108	journal	December 2010
Photodissociation of benzene under collision-free conditions: An ab initio /Rice–Ramsperger–Kassel–Marcus study Kislov, V. V.; Nguyen, T. L.; Mebel, A. M. The Journal of Chemical Physics, Vol. 120, Issue 15 https://doi.org/10.1063/1.1676275	journal	April 2004
Combustion chemistry probed by synchrotron VUV photoionization mass spectrometry Qi, Fei Proceedings of the Combustion Institute, Vol. 34, Issue 1 https://doi.org/10.1016/j.proci.2012.09.002	journal	January 2013
Extended High Circular Polarization in the Orion Massive Star Forming Region: Implications for the Origin of Homochirality in the Solar System Fukue, Tsubasa; Tamura, Motohide; Kandori, Ryo Origins of Life and Evolution of Biospheres, Vol. 40, Issue 3 https://doi.org/10.1007/s11084-010-9206-1	journal	March 2010
Gas phase synthesis of [4]-helicene Zhao, Long; Kaiser, Ralf I.; Xu, Bo Nature Communications, Vol. 10, Issue 1 https://doi.org/10.1038/s41467-019-09224-8	journal	April 2019
TD-¹HNMR Measurements Show Enantioselective Dissociation of Ribose and Glucose in the Presence of H₂¹⁷O Scorei, Romulus Ion; Cimpoiaşu, Vily Marius; Popa, Radu Astrobiology, Vol. 7, Issue 5 https://doi.org/10.1089/ast.2006.0076	journal	October 2007
Racemic amino acids from the ultraviolet photolysis of interstellar ice analogues Bernstein, Max P.; Dworkin, Jason P.; Sandford, Scott A. Nature, Vol. 416, Issue 6879 https://doi.org/10.1038/416401a	journal	March 2002
Deuterium Fractionation During Amino acid Formation by Photolysis of Interstellar ice Analogs Containing Deuterated Methanol Oba, Yasuhiro; Takano, Yoshinori; Watanabe, Naoki The Astrophysical Journal, Vol. 827, Issue 1 https://doi.org/10.3847/2041-8205/827/1/L18	journal	August 2016
Chirally Sensitive Electron-Induced Molecular Breakup and the Vester-Ulbricht Hypothesis Dreiling, J. M.; Gay, T. J. Physical Review Letters, Vol. 113, Issue 11 https://doi.org/10.1103/PhysRevLett.113.118103	journal	September 2014
Chirality Amplified: Long, Discrete Helicene Nanoribbons Xiao, Xiao; Pedersen, Stephan K.; Aranda, Daniel Journal of the American Chemical Society, Vol. 143, Issue 2 https://doi.org/10.1021/jacs.0c11260	journal	December 2020
UV photolysis, organic molecules in young disks, and the origin of meteoritic amino acids Throop, Henry B. Icarus, Vol. 212, Issue 2 https://doi.org/10.1016/j.icarus.2011.01.002	journal	April 2011
Chiroptical Properties of Symmetric Double, Triple, and Multiple Helicenes Mori, Tadashi Chemical Reviews, Vol. 121, Issue 4 https://doi.org/10.1021/acs.chemrev.0c01017	journal	January 2021
Crossed beam reaction of cyano radicals with hydrocarbon molecules. I. Chemical dynamics of cyanobenzene (C6H5CN; X 1A1) and perdeutero cyanobenzene (C6D5CN; X 1A1) formation from reaction of CN(X 2Σ+) with benzene C6H6(X 1A1g), and d6-benzene C6D6(X 1A1g) Balucani, N.; Asvany, O.; Chang, A. H. H. The Journal of Chemical Physics, Vol. 111, Issue 16 https://doi.org/10.1063/1.480070	journal	October 1999
Gaussian-3 theory using coupled cluster energies Curtiss, Larry A.; Raghavachari, Krishnan; Redfern, Paul C. Chemical Physics Letters, Vol. 314, Issue 1-2 https://doi.org/10.1016/S0009-2614(99)01126-4	journal	November 1999
Carbonaceous Chondrite Meteorites: the Chronicle of a Potential Evolutionary Path between Stars and Life Pizzarello, Sandra; Shock, Everett Origins of Life and Evolution of Biospheres, Vol. 47, Issue 3 https://doi.org/10.1007/s11084-016-9530-1	journal	January 2017
Enrichment of the amino acid L-isovaline by aqueous alteration on CI and CM meteorite parent bodies Glavin, D. P.; Dworkin, J. P. Proceedings of the National Academy of Sciences, Vol. 106, Issue 14 https://doi.org/10.1073/pnas.0811618106	journal	March 2009
The Formation of Nitriles in Hydrocarbon-Rich Atmospheres of Planets and Their Satellites: Laboratory Investigations by the Crossed Molecular Beam Technique Kaiser, Ralf I.; Balucani, Nadia Accounts of Chemical Research, Vol. 34, Issue 9 https://doi.org/10.1021/ar000112v	journal	September 2001
The Search for Chiral Asymmetry as a Potential Biosignature in our Solar System Glavin, Daniel P.; Burton, Aaron S.; Elsila, Jamie E. Chemical Reviews, Vol. 120, Issue 11 https://doi.org/10.1021/acs.chemrev.9b00474	journal	November 2019
Isotopic evidence for extraterrestrial non- racemic amino acids in the Murchison meteorite Engel, M. H.; Macko, S. A. Nature, Vol. 389, Issue 6648 https://doi.org/10.1038/38460	journal	September 1997
Detection of two interstellar polycyclic aromatic hydrocarbons via spectral matched filtering McGuire, Brett A.; Loomis, Ryan A.; Burkhardt, Andrew M. Science, Vol. 371, Issue 6535 https://doi.org/10.1126/science.abb7535	journal	March 2021
A Detailed Study of the Amino Acids Produced from the Vacuum UV Irradiation of Interstellar Ice Analogs Nuevo, Michel; Auger, Geneviève; Blanot, Didier Origins of Life and Evolution of Biospheres, Vol. 38, Issue 1 https://doi.org/10.1007/s11084-007-9117-y	journal	January 2008
On the Formation of Dipeptides in Interstellar Model ices Kaiser, R. I.; Stockton, A. M.; Kim, Y. S. The Astrophysical Journal, Vol. 765, Issue 2 https://doi.org/10.1088/0004-637X/765/2/111	journal	February 2013
Gaussian-3 (G3) theory for molecules containing first and second-row atoms Curtiss, Larry A.; Raghavachari, Krishnan; Redfern, Paul C. The Journal of Chemical Physics, Vol. 109, Issue 18 https://doi.org/10.1063/1.477422	journal	November 1998
Gaussian-3 theory using density functional geometries and zero-point energies Baboul, Anwar G.; Curtiss, Larry A.; Redfern, Paul C. The Journal of Chemical Physics, Vol. 110, Issue 16 https://doi.org/10.1063/1.478676	journal	April 1999
A Unified Mechanism on the Formation of Acenes, Helicenes, and Phenacenes in the Gas Phase Zhao, Long; Kaiser, Ralf I.; Xu, Bo Angewandte Chemie International Edition, Vol. 59, Issue 10 https://doi.org/10.1002/anie.201913037	journal	January 2020
Extraterrestrial prebiotic molecules: photochemistry vs. radiation chemistry of interstellar ices Arumainayagam, Chris R.; Garrod, Robin T.; Boyer, Michael C. Chemical Society Reviews, Vol. 48, Issue 8 https://doi.org/10.1039/C7CS00443E	journal	January 2019

Similar Records

A combined experimental and computational study on the reaction dynamics of the 1-propynyl (CH₃CC, X²A₁) – propylene (CH₃CHCH₂, X¹A') system: formation of 1,3-dimethylvinylacetylene (CH₃CCCHCHCH₃, X¹A') under single collision conditions

Journal Article · Thu Jul 20 00:00:00 EDT 2023 · Molecular Physics · OSTI ID:2325993

Medvedkov, Iakov A.; Nikolayev, Anatoliy A.; He, Chao; +3 more

Formation of Benzene and Naphthalene through Cyclopentadienyl-Mediated Radical–Radical Reactions

Journal Article · Thu Dec 30 00:00:00 EST 2021 · Journal of Physical Chemistry Letters · OSTI ID:2325993

Kaiser, Ralf I.; Zhao, Long; Lu, Wenchao; +4 more

A Unified Mechanism on the Formation of Acenes, Helicenes, and Phenacenes in the Gas Phase

Journal Article · Thu Jan 23 00:00:00 EST 2020 · Angewandte Chemie · OSTI ID:2325993

Zhao, Long; Kaiser, Ralf I.; Xu, Bo; +6 more

Related Subjects

37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY

Title: Gas-phase synthesis of racemic helicenes and their potential role in the enantiomeric enrichment of sugars and amino acids in meteorites

Citation Formats

References (56)

Similar Records

Related Subjects