Meteoritic Amino Acids: Diversity in Compositions Reflects Parent Body Histories
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The analysis of amino acids in meteorites dates back over 50 years; however, it is only in recent years that research has expanded beyond investigations of a narrow set of meteorite groups (exemplified by the Murchison meteorite) into meteorites of other types and classes. These new studies have shown a wide diversity in the abundance and distribution of amino acids across carbonaceous chondrite groups, highlighting the role of parent body processes and composition in the creation, preservation, or alteration of amino acids. Although most chiral amino acids are racemic in meteorites, the enantiomeric distribution of some amino acids, particularly of the nonprotein amino acid isovaline, has also been shown to vary both within certain meteorites and across carbonaceous meteorite groups. Large l-enantiomeric excesses of some extraterrestrial protein amino acids (up to ∼60%) have also been observed in rare cases and point to nonbiological enantiomeric enrichment processes prior to the emergence of life. In this Outlook, we review these recent meteoritic analyses, focusing on variations in abundance, structural distributions, and enantiomeric distributions of amino acids and discussing possible explanations for these observations and the potential for future work.
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Chondritic meteorite deposits contain small enantiomeric excesses toward L-amino acids.
“Evidence of small enantiomeric excesses toward L-amino acids found in chondritic meteorite deposits (Elsila et al. 2016)”
From The Origin of Biological Homochirality (2019) · cites this paper as Elsila et al. 2016
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Asymmetric autocatalysis and amplification of enantiomeric excess of a chiral molecule
Soai, K., Shibata, T., Morioka, H., & Choji, K. (1995) · Nature · doi:10.1038/378767a0 · Cited by 1,085 · see citing works
Organic compounds in carbonaceous meteorites
Sephton, M. A. (2002) · Natural Product Reports · doi:10.1039/b103775g · Cited by 704 · see citing works
Schmitt-Kopplin, P., Gabelica, Z., Gougeon, R. D., Fekete, A., Kanawati, B., Harir, M., Gebefuegi, I., Eckel, G., & Hertkorn, N. (2010) · Proceedings of the National Academy of Sciences · doi:10.1073/pnas.0912157107 · Cited by 594 · see citing works
Carbonaceous Meteorites Contain a Wide Range of Extraterrestrial Nucleobases
Callahan, M. P., Smith, K. E., Cleaves, H. J., Ruzicka, J., Stern, J. C., Glavin, D. P., House, C. H., & Dworkin, J. P. (2011) · Proceedings of the National Academy of Sciences · doi:10.1073/pnas.1106493108 · Cited by 590 · see citing works
Self-citationBurton, A. S., Stern, J. C., Elsila, J. E., Glavin, D. P., & Dworkin, J. P. (2012) · Chemical Society Reviews · doi:10.1039/c2cs35109a · Cited by 398 · see citing works
Self-citationThe mechanism of synthesis of amino acids by electric discharges
Miller, S. L. (1957) · Biochimica et Biophysica Acta · doi:10.1016/0006-3002(57)90366-9 · Cited by 380 · see citing works
Myrgorodska, I., Meinert, C., Martins, Z., Le Sergeant d'Hendecourt, L., & Meierhenrich, U. J. (2015) · Angewandte Chemie International Edition · doi:10.1002/anie.201409354 · Cited by 68 · see citing works
Anisotropy Spectra of Amino Acids
Meinert, C., Bredehöft, J. H., Filippi, J., Baraud, Y., Nahon, L., Wien, F., Jones, N. C., Hoffmann, S. V., & Meierhenrich, U. J. (2012) · Angewandte Chemie International Edition · doi:10.1002/anie.201108997 · Cited by 64 · see citing works
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Research works printed but not linked: 104
- Love S. G.; Brownlee D. E. A direct measurement of the terrestrial mass accretion rate of cosmic dust. Science 1993, 262, 550– 553. 10.1126/science.262.5133.550. 17733236 · DOI
- Degens E. T.; Bajor M. Amino acids and sugars in the Bruderheim and Murray meteorite. Naturwissenschaften 1962, 49, 605– 606. 10.1007/BF01178050. · DOI
- Pizzarello S.; Cronin J. R.; Flynn G. In Meteorites and the Early Solar System II; Lauretta D. S., Ed.; University of Arizona Press: Tucson, 2006.
- Kvenvolden K.; Lawless J.; Pering K.; Peterson E.; Flores J.; Ponnamperuma C.; Kaplan I. R.; Moore C. Evidence for extraterrestrial amino-acids and hydrocarbons in the Murchison meteorite. Nature 1970, 228, 923– 926. 10.1038/228923a0. 5482102 · DOI
- Oró J.; Gibert J.; Lichtenstein H.; Wikstrom S.; Flory D. A. Amino-acids, aliphatic and aromatic hydrocarbons in the Murchison meteorite. Nature 1971, 230, 105– 106. 10.1038/230105a0. 4927006 · DOI
- Pering K. L.; Ponnamperuma C. Aromatic hydrocarbons in the Murchison meteorite. Science 1971, 173, 237– 239. 10.1126/science.173.3993.237. 17741420 · DOI
- Studier M. H.; Hayatsu R.; Anders E. Origin of organic matter in the early solar system-V. Further studies of meteoritic hydrocarbons and a discussion of their origin. Geochim. Cosmochim. Acta 1972, 36, 189– 215. 10.1016/0016-7037(72)90006-3. · DOI
- Basile B. P.; Middleditch B. S.; Oró J. Polycyclic aromatic hydrocarbons in the Murchison meteorite. Org. Geochem. 1984, 5, 211– 216. 10.1016/0146-6380(84)90008-1. · DOI
- Naraoka H.; Shimoyama A.; Harada K. Isotopic evidence from an Antarctic carbonaceous chondrite for two reaction pathways of extraterrestrial PAH formation. Earth Planet. Sci. Lett. 2000, 184, 1– 7. 10.1016/S0012-821X(00)00316-2. · DOI
- Yuen G.; Blair N.; Des Marais D. J.; Chang S. Carbon isotope composition of low molecular weight hydrocarbons and monocarboxylic acids from Murchison meteorite. Nature 1984, 307, 252– 254. 10.1038/307252a0. 11536574 · DOI
- Huang Y.; Wang Y.; Alexandre M. R.; Lee T.; Rose-Petruck C.; Fuller M.; Pizzarello S. Molecular and compound-specific isotopic characterization of monocarboxylic acids in carbonaceous meteorites. Geochim. Cosmochim. Acta 2005, 69, 1073– 1084. 10.1016/j.gca.2004.07.030. · DOI · Paper page
- Aponte J. C.; Alexandre M. R.; Wang Y.; Brearley A. J.; Alexander C. M. O'D.; Huang Y. Effects of secondary alteration on the composition of free and IOM-derived monocarboxylic acids in carbonaceous chondrites. Geochim. Cosmochim. Acta 2011, 75, 2309– 2323. 10.1016/j.gca.2011.01.040. · DOI
- Peltzer E. T.; Bada J. L. Alpha-hydroxycarboxylic acids in the Murchison meteorite. Nature 1978, 272, 443– 444. 10.1038/272443a0. · DOI
- Pizzarello S.; Wang Y.; Chaban G. M. A comparative study of the hydroxy acids from the Murchison, GRA 95229 and LAP 02342 meteorites. Geochim. Cosmochim. Acta 2010, 74, 6206– 6217. 10.1016/j.gca.2010.08.013. · DOI · Paper page
- Cooper G.; Kimmich N.; Belisle W.; Sarinana J.; Brabham K.; Garrel L. Carbonaceous meteorites as a source of sugar-related organic compounds for the early Earth. Nature 2001, 414, 879– 883. 10.1038/414879a. 11780054 · DOI
- Lawless J. G.; Kvenvolden K. A.; Peterson E.; Ponnamperuma C.; Moore C. Amino acids indigenous to Murray meteorite. Science 1971, 173, 626– 627. 10.1126/science.173.3997.626. 17833108 · DOI
- Ehrenfreund P.; Glavin D. P.; Botta O.; Cooper G.; Bada J. L. Extraterrestrial amino acids in Orgueil and Ivuna: Tracing the parent body of Cl type carbonaceous chondrites. Proc. Natl. Acad. Sci. U. S. A. 2001, 98, 2138– 2141. 10.1073/pnas.051502898. 11226205 PMC30105 · DOI
- Cronin J. R.; Moore C. B. Amino acid analyses of the Murchison, Murray, and Allende carbonaceous chondrites. Science 1971, 172, 1327– 1329. 10.1126/science.172.3990.1327. 17755206 · DOI
- Martins Z.; Alexander C. M. O'D.; Orzechowska G. E.; Fogel M. L.; Ehrenfreund P. Indigenous amino acids in primitive CR meteorites. Meteorit. Planet. Sci. 2007, 42, 2125– 2136. 10.1111/j.1945-5100.2007.tb01013.x. · DOI
- Jungclaus G. A.; Yuen G. U.; Moore C. B.; Lawless J. G. Evidence for the presence of low molecular weight alcohols and carbonyl compounds in the Murchison meteorite. Meteoritics 1976, 11, 231– 237. 10.1111/j.1945-5100.1976.tb00324.x. · DOI
- Jungclaus G.; Cronin J. R.; Moore C. B.; Yuen G. U. Aliphatic amines in the Murchison meteorite. Nature 1976, 261, 126– 128. 10.1038/261126a0. · DOI
- Cronin J. R.; Chang S. In The Chemistry of Life’s Origins; Greenberg J. M.; Mendoza C. X.; Pirronelle V., Eds.; Kluwer Academic Publishers: Dordrecht, 1993; Vol. 416.
- Sephton M. A.; Gilmour I. Compound-specific isotope analysis of the organic constituents in carbonaceous chondrites. Mass Spectrom. Rev. 2001, 20, 111– 120. 10.1002/mas.1006. 11746344 · DOI
- Elsila J. E.; Charnley S. B.; Burton A. S.; Glavin D. P.; Dworkin J. P. Compound-specific carbon, nitrogen, and hydrogen isotopic ratios for amino acids in CM and CR chondrites and their use in evaluating potential formation pathways. Meteorit. Planet. Sci. 2012, 47, 1517– 1536. 10.1111/j.1945-5100.2012.01415.x. · DOI
- Weisberg M. K.; McCoy T. J.; Krot A. N. In Meteorites and the Early Solar System II, 2nd ed.; Lauretta D. S., McSween H. Y. Jr., Eds.; University of Arizona Press: Tucson, 2006.
- Sears D. W. G.; Dodd R. T. In Meteorites and the Early Solar System; Kerridge J. F., Matthews M. S., Eds.; The University of Arizona Press: Tucson, 1988.
- Huss G. R.; Rubin A. E.; Grossman J. N. In Meteorites and the Early Solar System II, 2nd ed.; Lauretta D. S., McSween H. Y. Jr., Eds.; University of Arizona Press: Tucson, 2006.
- Brearley A. J. In Meteorites and the Early Solar System II, 2nd ed.; Lauretta D. S.; McSween H. Y. Jr., Eds.; University of Arizona Press: Tucson, 2006.
- Lawless J. G.; Kvenvolden K. A.; Peterson E.; Ponnamperuma C.; Jarosewich E. Physical sciences: Evidence for amino-acids of extraterrestrial origin in the Orgueil meteorite. Nature 1972, 236, 66– 67. 10.1038/236066a0. · DOI
- Cronin J. R.; Pizzarello S. Amino acids in meteorites. Adv. Space Res. 1983, 3, 5– 18. 10.1016/0273-1177(83)90036-4. 11542462 · DOI
- Pizzarello S.; Cronin J. R. Non-racemic amino acids in the Murray and Murchison meteorites. Geochim. Cosmochim. Acta 2000, 64, 329– 338. 10.1016/S0016-7037(99)00280-X. 11543420 · DOI · Paper page
- Botta O.; Glavin D. P.; Kminek G.; Bada J. L. Relative amino acid concentrations as a signature for parent body processes of carbonaceous chondrites. Origins Life Evol. Biospheres 2002, 32, 143– 163. 10.1023/A:1016019425995. 12185673 · DOI
- Glavin D. P.; Dworkin J. P.; Aubrey A.; Botta O.; Doty J. H.; Martins Z.; Bada J. L. Amino acid analyses of Antarctic CM2 meteorites using liquid chromatography-time of flight-mass spectrometry. Meteorit. Planet. Sci. 2006, 41, 889– 902. 10.1111/j.1945-5100.2006.tb00493.x. · DOI
- Pizzarello S.; Huang Y.; Alexandre M. R. Molecular asymmetry in extraterrestrial chemistry: Insights from a pristine meteorite. Proc. Natl. Acad. Sci. U. S. A. 2008, 105, 3700– 3704. 10.1073/pnas.0709909105. 18310323 PMC2268819 · DOI · Paper page
- Glavin D. P.; Dworkin J. P. Enrichment of the amino acid L-isovaline by aqueous alteration on CI and CM meteorite parent bodies. Proc. Natl. Acad. Sci. U. S. A. 2009, 106, 5487– 5492. 10.1073/pnas.0811618106. 19289826 PMC2667035 · DOI · Paper page
- Pizzarello S.; Holmes W. Nitrogen-containing compounds in two CR2 meteorites: 15N composition, molecular distribution and precursor molecules. Geochim. Cosmochim. Acta 2009, 73, 2150– 2162. 10.1016/j.gca.2009.01.022. · DOI
- Glavin D. P.; Callahan M. P.; Dworkin J. P.; Elsila J. E. The effects of parent body processes on amino acids in carbonaceous chondrites. Meteorit. Planet. Sci. 2010, 45, 1948– 1972. 10.1111/j.1945-5100.2010.01132.x. · DOI
- Pizzarello S.; Groy T. L. Molecular asymmetry in extraterrestrial organic chemistry: An analytical perspective. Geochim. Cosmochim. Acta 2011, 75, 645– 656. 10.1016/j.gca.2010.10.025. · DOI
- Burton A. S.; Glavin D. P.; Callahan M. P.; Dworkin J. P.; Jenniskens P.; Shaddad M. H. Heterogeneous distributions of amino acids provide evidence of multiple sources within the Almahata Sitta parent body, asteroid 2008 TC3. Meteorit. Planet. Sci. 2011, 46, 1703– 1712. 10.1111/j.1945-5100.2011.01257.x. · DOI
- Burton A. S.; Elsila J. E.; Callahan M. P.; Martin M. G.; Glavin D. P.; Johnson N. M.; Dworkin J. P. A propensity for n-ω-amino acids in thermally altered Antarctic meteorites. Meteorit. Planet. Sci. 2012, 47, 374– 386. 10.1111/j.1945-5100.2012.01341.x. · DOI
- Chan H. S.; Martins Z.; Sephton M. A. Amino acid analyses of type 3 chondrites Colony, Ornans, Chainpur, and Bishunpur. Meteorit. Planet. Sci. 2012, 47, 1502– 1516. 10.1111/j.1945-5100.2012.01413.x. · DOI
- Burton A. S.; Elsila J. E.; Hein J. E.; Glavin D. P.; Dworkin J. P. Extraterrestrial amino acids identified in metal-rich CH and CB carbonaceous chondrites from Antarctica. Meteorit. Planet. Sci. 2013, 48, 390– 402. 10.1111/maps.12063. · DOI
- Burton A. S.; Grunsfeld S.; Elsila J. E.; Glavin D. P.; Dworkin J. P. The effects of parent-body hydrothermal heating on amino acid abundances in CI-like chondrites. Polar Sci. 2014, 8, 255– 263. 10.1016/j.polar.2014.05.002. · DOI
- Burton A. S.; McLain H.; Glavin D. P.; Elsila J. E.; Davidson J.; Miller K. E.; Andronikov A. V.; Lauretta D.; Dworkin J. P. Amino acid analyses of R and CK chondrites. Meteorit. Planet. Sci. 2015, 50, 470– 482. 10.1111/maps.12433. · DOI
- Martins Z.; Modica P.; Zanda B.; d’Hendecourt L. L. S. The amino acid and hydrocarbon contents of the Paris meteorite: Insights into the most primitive CM chondrite. Meteorit. Planet. Sci. 2015, 50, 926– 943. 10.1111/maps.12442. · DOI
- Chan Q.; Chikaraishi Y.; Takano Y.; Ogawa N.; Ohkouchi N. Amino acid compositions in heated carbonaceous chondrites and their compound-specific nitrogen isotopic ratios. Earth, Planets Space 2016, 68, 7 10.1186/s40623-016-0382-8. · DOI
- Horan J. R. The Murray, Calloway County, Kentucky, aerolite (CN = +0881,366)*. Meteoritics 1953, 1, 114– 121. 10.1111/j.1945-5100.1953.tb01322.x. · DOI
- Corrigan C. M.; Welzenbach L. C.; Righter K.; McBride K. M.; McCoy T. J.; Harvey R. P.; Satterwhite C. E. In 35 Seasons of U.S. Antarctic Meteorites (1976–2010); John Wiley & Sons, Inc.: Hoboken, 2014.
- Callahan M. P.; Martin M. G.; Burton A. S.; Glavin D. P.; Dworkin J. P. Amino acid analysis in micrograms of meteorite sample by nanoliquid chromatography-high-resolution mass spectrometry. J. Chromatog. A 2014, 1332, 30– 34. 10.1016/j.chroma.2014.01.032. 24529954 · DOI
- Matrajt G.; Pizzarello S.; Taylor S.; Brownlee D. Concentration and variability of the AIB amino acid in polar micrometeorites: Implications for the exogenous delivery of amino acids to the primitive Earth. Meteorit. Planet. Sci. 2004, 39, 1849– 1858. 10.1111/j.1945-5100.2004.tb00080.x. · DOI
- Martins Z.; Sephton M. A. In Amino Acids, Peptides and Proteins in Organic Chemistry. Vol. 1—Origins and Synthesis of Amino Acids; Hughes A. B., Ed.; Wiley: Weinheim, Germany, 2009.
- Burton A. S.; Glavin D. P.; Elsila J. E.; Dworkin J. P.; Jenniskens P.; Yin Q. Z. The amino acid composition of the Sutter’s Mill CM2 carbonaceous chondrite. Meteorit. Planet. Sci. 2014, 49, 2074– 2086. 10.1111/maps.12281. · DOI
- Rodante F. Thermodynamics and kinetics of decomposition processes for standard α-amino acids and some of their dipeptides in the solid state. Thermochim. Acta 1992, 200, 47– 61. 10.1016/0040-6031(92)85105-5. · DOI
- McCollom T. M. The influence of minerals on decomposition of the n-alkyl-α-amino acid norvaline under hydrothermal conditions. Geochim. Cosmochim. Acta 2013, 104, 330– 357. 10.1016/j.gca.2012.11.008. · DOI
- Callahan M. P.; Burton A. S.; Elsila J. E.; Baker E. M.; Smith K. E.; Glavin D. P.; Dworkin J. P. A search for amino acids and nucleobases in the Martian meteorite Roberts Massif 04262 using liquid chromatography-mass spectrometry. Meteorit. Planet. Sci. 2013, 48, 786– 795. 10.1111/maps.12103. · DOI
- Peltzer E. T.; Bada J. L.; Schlesinger G.; Miller S. L. The chemical conditions on the parent body of the Murchison meteorite: some conclusions based on amino, hydroxy and dicarboxylic acids. Adv. Space Res. 1984, 4, 69– 74. 10.1016/0273-1177(84)90546-5. 11537797 · DOI
- Lerner N. R.; Cooper G. W. Iminodicarboxylic acids in the Murchison meteorite: Evidence of Strecker reactions. Geochim. Cosmochim. Acta 2005, 69, 2901– 2906. 10.1016/j.gca.2004.12.024. · DOI
- Cooper G. W.; Cronin J. R. Linear and cyclic aliphatic carboxamides of the Murchison meteorite: Hydrolyzable derivatives of amino acids and other carboxylic acids. Geochim. Cosmochim. Acta 1995, 59, 1003– 1015. 10.1016/0016-7037(95)00018-6. 11540047 · DOI
- Meierhenrich U. J.; Muñoz Caro G. M.; Bredehöft J. H.; Jessberger E. K.; Thiemann W. H.-P. Identification of diamino acids in the Murchison meteorite. Proc. Natl. Acad. Sci. U. S. A. 2004, 101, 9182– 9186. 10.1073/pnas.0403043101. 15194825 PMC438950 · DOI
- Bernstein M. P.; Dworkin J. P.; Sandford S. A.; Cooper G. W.; Allamandola L. J. Racemic amino acids from the ultraviolet photolysis of interstellar ice analogues. Nature 2002, 416, 401– 403. 10.1038/416401a. 11919623 · DOI
- Muñoz Caro G. M.; Meierhenrich U. J.; Schutte W. A.; Barbier B.; Arcones Segovia A.; Rosenbauer H.; Thiemann W. H.-P.; Brack A.; Greenberg J. M. Amino acids from ultraviolet irradiation of interstellar ice analogues. Nature 2002, 416, 403– 406. 10.1038/416403a. 11919624 · DOI
- Hudson R. L.; Lewis A. S.; Moore M. H.; Dworkin J. P.; Martin M. G. Enigmatic isovaline: Investigating the stability, racemization, and formation of a non-biological amino acid. In Bioastronomy 2007: Molecules, Microbes, and Extraterrestrial Life; Meech K. J., Keane J. V., Mumma M. J., Siefert J. L., Werthimer D. J., Eds.; Astronomical Society of the Pacific: San Francisco, 2009; Vol. 420, pp 157– 162.
- Hayatsu R.; Studier M. H.; Anders E. Origin of organic matter in early solar system -- IV. Amino acids: Confirmation of catalytic synthesis by mass spectrometry. Geochim. Cosmochim. Acta 1971, 35, 939– 951. 10.1016/0016-7037(71)90007-X. · DOI
- Yoshino D.; Hayatsu R.; Anders E. Origin of organic matter in early solar system - III. Amino acids: Catalytic synthesis. Geochim. Cosmochim. Acta 1971, 35, 927– 938. 10.1016/0016-7037(71)90006-8. · DOI
- Pizzarello S. Catalytic syntheses of amino acids and their significance for nebular and planetary chemistry. Meteorit. Planet. Sci. 2012, 47, 1291– 1296. 10.1111/j.1945-5100.2012.01390.x. · DOI
- Herbst E. Chemistry in the Interstellar Medium. Annu. Rev. Phys. Chem. 1995, 46, 27– 54. 10.1146/annurev.pc.46.100195.000331. · DOI
- Pizzarello S.; Shock E. The organic composition of carbonaceous meteorites: the evolutionary story ahead of biochemistry. Cold Spring Harbor Perspect. Biol. 2010, 2, a002105 10.1101/cshperspect.a002105. PMC2829962 20300213 · DOI · Paper page
- Aponte J. C.; Dworkin J. P.; Elsila J. E. Assessing the origins of aliphatic amines in the Murchison meteorite from their compound-specific carbon isotopic ratios and enantiomeric composition. Geochim. Cosmochim. Acta 2014, 141, 331– 345. 10.1016/j.gca.2014.06.035. · DOI
- Aponte J. C.; Dworkin J. P.; Elsila J. E. Molecular distribution of aliphatic amines in Antarctic CR2 and CM2 carbonaceous chondrites. 47th Lunar Planet. Sci. Conf. 2016, 1039.
- Beshore E.; Sutter B.; Mink R.; Lauretta D.; Moreau M.; Boynton W.; Dworkin J.; Everett D.; Shinohara C.; Gal-Edd J. The OSIRIS-REx asteroid sample return mission. 2015 IEEE Aerospace Conf. 2015, 1– 14. 10.1109/AERO.2015.7118989. · DOI
- Tsuda Y.; Yoshikawa M.; Abe M.; Minamino H.; Nakazawa S. System design of the Hayabusa 2—Asteroid sample return mission to 1999 JU3. Acta Astronaut. 2013, 91, 356– 362. 10.1016/j.actaastro.2013.06.028. · DOI
- Bonner W. A. Chirality and life. Origins Life Evol. Biospheres 1995, 25, 175– 190. 10.1007/BF01581581. 11536669 · DOI · Paper page
- Milton R. C.; Milton S. C.; Kent S. B. Total chemical synthesis of a D-enzyme: the enantiomers of HIV-1 protease show reciprocal chiral substrate specificity. Science 1992, 256, 1445– 1448. 10.1126/science.1604320. 1604320 · DOI
- Bada J. L. Origins of homochirality. Nature 1995, 374, 594– 595. 10.1038/374594a0. 7536302 · DOI
- Cronin J. R.; Pizzarello S. Enantiomeric excesses in meteoritic amino acids. Science 1997, 275, 951– 955. 10.1126/science.275.5302.951. 9020072 · DOI · Paper page
- Herd C. D. K.; Blinova A.; Simkus D. N.; Huang Y. S.; Tarozo R.; Alexander C. M. O'D.; Gyngard F.; Nittler L. R.; Cody G. D.; Fogel M. L.; et al. Origin and evolution of prebiotic organic matter as inferred from the Tagish Lake meteorite. Science 2011, 332, 1304– 1307. 10.1126/science.1203290. 21659601 · DOI
- Glavin D. P.; Elsila J. E.; Burton A. S.; Callahan M. P.; Dworkin J. P.; Hilts R. W.; Herd C. D. K. Unusual nonterrestrial L-proteinogenic amino acid excesses in the Tagish Lake meteorite. Meteorit. Planet. Sci. 2012, 47, 1347– 1364. 10.1111/j.1945-5100.2012.01400.x. · DOI
- Pizzarello S.; Schrader D. L.; Monroe A. A.; Lauretta D. S. Large enantiomeric excesses in primitive meteorites and the diverse effects of water in cosmochemical evolution. Proc. Natl. Acad. Sci. U. S. A. 2012, 109, 11949– 11954. 10.1073/pnas.1204865109. 22778439 PMC3409747 · DOI
- Elsila J. E.; Glavin D. P.; Dworkin J. P.; Martins Z.; Bada J. L. Inconclusive evidence for nonterrestrial isoleucine enantiomeric excesses in primitive meteorites. Proc. Natl. Acad. Sci. U. S. A. 2012, 109, E3288– E3288. 10.1073/pnas.1213261109. 23064644 PMC3511738 · DOI
- Cohen B. A.; Chyba C. F. Racemization of meteoritic amino acids. Icarus 2000, 145, 272– 281. 10.1006/icar.1999.6328. · DOI
- Bonner W. A.; Rubenstein E. Supernovae, neutron-stars and biomolecular chirality. BioSystems 1987, 20, 99– 111. 10.1016/0303-2647(87)90025-6. 3580540 · DOI · Paper page
- Rosenberg R. A.; Abu Haija M.; Ryan P. J. Chiral-selective chemistry induced by spin-polarized secondary electrons from a magnetic substrate. Phys. Rev. Lett. 2008, 101, 178301 10.1103/PhysRevLett.101.178301. 18999792 · DOI · Paper page
- Flores J. J.; Bonner W. A.; Massey G. A. Asymmetric photolysis of (RS)-leucine with circularly polarized ultraviolet light. J. Am. Chem. Soc. 1977, 99, 3622– 3625. 10.1021/ja00453a018. 858868 · DOI · Paper page
- Takano Y.; Takahashi J.; Kaneko T.; Marumo K.; Kobayashi K. Asymmetric synthesis of amino acid precursors in interstellar complex organics by circularly polarized light. Earth Planet. Sci. Lett. 2007, 254, 106– 114. 10.1016/j.epsl.2006.11.030. · DOI
- de Marcellus P.; Meinert C.; Nuevo M.; Filippi J.-J.; Danger G.; Deboffle D.; Nahon L.; d’Hendecourt L. L. S.; Meierhenrich U. J. Non-racemic amino acid production by ultraviolet irradiation of achiral interstellar ice analogs with circularly polarized light. Astrophys. J., Lett. 2011, 727, L27 10.1088/2041-8205/727/2/L27. · DOI
- Meinert C.; Hoffmann S. V.; Cassam-Chenaï P.; Evans A. C.; Giri C.; Nahon L.; Meierhenrich U. J. Photonenergy-controlled symmetry breaking with circularly polarized light. Angew. Chem., Int. Ed. 2014, 53, 210– 214. 10.1002/anie.201307855. 24227543 · DOI · Paper page
- Modica P.; Meinert C.; Marcellus P. d.; Nahon L.; Meierhenrich U. J.; d’Hendecourt L. L. S. Enantiomeric excesses induced in amino acids by ultraviolet circularly polarized light irradiation of extraterrestrial ice analogs: A possible source of asymmetry for prebiotic chemistry. Astrophys. J. 2014, 788, 79 10.1088/0004-637X/788/1/79. · DOI
- Kondepudi D. K.; Kaufman R. J.; Singh N. Chiral symmetry breaking in sodium chlorate crystallization. Science 1990, 250, 975– 976. 10.1126/science.250.4983.975. 17746924 · DOI · Paper page
- Blackmond D. G. Asymmetric autocatalysis and its implications for the origin of homochirality. Proc. Natl. Acad. Sci. U. S. A. 2004, 101, 5732– 5736. 10.1073/pnas.0308363101. 15067112 PMC395976 · DOI · Paper page
- Klussmann M.; White A. J. P.; Armstrong A.; Blackmond D. G. Rationalization and prediction of solution enantiomeric excess in ternary phase systems. Angew. Chem., Int. Ed. 2006, 45, 7985– 7989. 10.1002/anie.200602520. 16986192 · DOI
- Kawasaki T.; Hatase K.; Fujii Y.; Jo K.; Soai K.; Pizzarello S. The distribution of chiral asymmetry in meteorites: An investigation using asymmetric autocatalytic chiral sensors. Geochim. Cosmochim. Acta 2006, 70, 5395– 5402. 10.1016/j.gca.2006.08.006. · DOI
- Hein J. E.; Blackmond D. G. On the origin of single chirality of amino acids and sugars in biogenesis. Acc. Chem. Res. 2012, 45, 2045– 2054. 10.1021/ar200316n. 22353168 · DOI
- Frank F. C. On spontaneous asymmetric synthesis. Biochim. Biophys. Acta 1953, 11, 459– 463. 10.1016/0006-3002(53)90082-1. 13105666 · DOI · Paper page
- Viedma C. Enantiomeric crystallization from DL-aspartic and DL-glutamic acids: Implications for biomolecular chirality in the origin of life. Origins Life Evol. Biospheres 2001, 31, 501– 509. 10.1023/A:1012790523136. 11770258 · DOI
- Viedma C.; Ortiz J. E.; Torres T. d.; Izumi T.; Blackmond D. G. Evolution of solid phase homochirality for a proteinogenic amino acid. J. Am. Chem. Soc. 2008, 130, 15274– 15275. 10.1021/ja8074506. 18954052 · DOI · Paper page
- Blinova A. I.; Zega T. J.; Herd C. D. K.; Stroud R. M. Testing variations within the Tagish Lake meteorite—I: Mineralogy and petrology of pristine samples. Meteorit. Planet. Sci. 2014, 49, 473– 502. 10.1111/maps.12271. · DOI
- Greshake A.; Krot A. N.; Meibom A.; Weisberg M. K.; Zolensky M. E.; Keil K. Heavily-hydrated lithic clasts in CH chondrites and the related, metal-rich chondrites Queen Alexandra Range 94411 and Hammadah al Hamra 237. Meteorit. Planet. Sci. 2002, 37, 281– 293. 10.1111/j.1945-5100.2002.tb01110.x. · DOI
- Aponte J. C.; Tarozo R.; Alexandre M. R.; Alexander C. M. O'D.; Charnley S. B.; Hallmann C.; Summons R. E.; Huang Y. Chirality of meteoritic free and IOM-derived monocarboxylic acids and implications for prebiotic organic synthesis. Geochim. Cosmochim. Acta 2014, 131, 1– 12. 10.1016/j.gca.2014.01.035. · DOI
- Aponte J. C.; Dworkin J. P.; Elsila J. E. Indigenous aliphatic amines in the aqueously altered Orgueil meteorite. Meteorit. Planet. Sci. 2015, 50, 1733– 1749. 10.1111/maps.12507. · DOI
- Meinert C.; Jones N. C.; Hoffmann S. V.; Meierhenrich U. J. Anisotropy spectroscopy of chiral alcohols, amines, and monocarboxylic acids: Implications for the analyses of extraterrestrial samples. J. Photochem. Photobiol., A 2016, 10.1016/j.jphotochem.2015.12.018. · DOI
- Gómez-Bombarelli R.; González-Pérez M.; Pérez-Prior M. T.; Calle E.; Casado J. Computational Study of the Acid Dissociation of Esters and Lactones. A Case Study of Diketene. J. Org. Chem. 2009, 74, 4943– 4948. 10.1021/jo900645h. 19459649 · DOI
- Bordwell F. G. Equilibrium acidities in dimethyl sulfoxide solution. Acc. Chem. Res. 1988, 21, 456– 463. 10.1021/ar00156a004. · DOI
- Stroud E. D.; Fife D. J.; Smith G. G. A method for the determination of the pKa of the.alpha.-hydrogen in amino acids using racemization and exchange studies. J. Org. Chem. 1983, 48, 5368– 5369. 10.1021/jo00174a045. · DOI
- Bordwell F. G.; Drucker G. E.; Fried H. E. Acidities of carbon and nitrogen acids: the aromaticity of the cyclopentadienyl anion. J. Org. Chem. 1981, 46, 632– 635. 10.1021/jo00316a032. · DOI
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- Authors
- Elsila, J. E., Aponte, J. C., Blackmond, D. G., Burton, A. S., Dworkin, J. P., & Glavin, D. P.
- Affiliations
- Goddard Space Flight Center (US)
- Scripps Research Institute (US)
- National Aeronautics and Space Administration (US)
- Corresponding author
- Elsila, Jamie E.
- ORCID
- Venue
- ACS Central Science
- Publisher
- American Chemical Society (ACS)
- Published
- 2016-04-25
- Volume
- 2
- Issue
- 6
- Pages
- 370-379
- ISSN
- 2374-7943 (ISSN-L)
- 2374-7951
- PMC
- PMC4919777
- OpenAlex
- W2343689880
- Cited by
- 187
- References
- 8
- Citations by year
- 2026: 16 · 2025: 20 · 2024: 21 · 2023: 26 · 2022: 20 · 2021: 17 · 2020: 20 · 2019: 18 · 2018: 20 · 2017: 8 · 2016: 1
- FWCI
- 0.96
- Type
- journal article
- Language
- en
- Open access
- diamond
- doi.org
- Licence
- Locations
- ACS Central Science (publishedVersion, other-oa)
- PubMed Central (publishedVersion)
- PubMed (publishedVersion)
- DOAJ (DOAJ: Directory of Open Access Journals) (submittedVersion, cc-by-sa)
- Funders
- National Aeronautics and Space Administration
- Goddard Space Flight Center (13-13NAI7-0032)
- Simons Foundation (SCOL 287625, SCOL 302497)
- Topics
- Physical Sciences › Physics and Astronomy › Astronomy and Astrophysics › Origins and Evolution of Life
- Physical Sciences › Physics and Astronomy › Astronomy and Astrophysics › Astro and Planetary Science
- Physical Sciences › Physics and Astronomy › Astronomy and Astrophysics › Space Science and Extraterrestrial Life
- Keywords
- meteoritic amino acids, carbonaceous chondrites, enantiomeric excess, isovaline, nonprotein amino acids, racemization, origin of life, Murchison meteorite
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