Hostname: page-component-78c5997874-4rdpn Total loading time: 0 Render date: 2024-11-13T00:44:00.988Z Has data issue: false hasContentIssue false
  • English
  • Français

Stability of non-proteinogenic amino acids to UV and gamma irradiation

Published online by Cambridge University Press:  08 October 2018

Laura Rowe ,
Julie Peller ,
Claire Mammoser ,
Kelly Davidson ,
Amy Gunter ,
Bayland Brown  and
Shilpa Dhar
Laura Rowe*
Affiliation:
Department of Chemistry, Valparaiso University, 1710 Chapel Drive, Valparaiso, IN 46383, USA
Julie Peller
Affiliation:
Department of Chemistry, Valparaiso University, 1710 Chapel Drive, Valparaiso, IN 46383, USA Radiation Laboratory, University of Notre Dame, Notre Dame, IN 46556, USA
Claire Mammoser
Affiliation:
Department of Chemistry, Valparaiso University, 1710 Chapel Drive, Valparaiso, IN 46383, USA
Kelly Davidson
Affiliation:
Department of Chemistry, Valparaiso University, 1710 Chapel Drive, Valparaiso, IN 46383, USA Ivy Tech Community College, 3100 Ivy Tech Drive, Valparaiso, IN, 46324, USA
Amy Gunter
Affiliation:
Department of Chemistry, Valparaiso University, 1710 Chapel Drive, Valparaiso, IN 46383, USA
Bayland Brown
Affiliation:
Ivy Tech Community College, 3100 Ivy Tech Drive, Valparaiso, IN, 46324, USA
Shilpa Dhar
Affiliation:
Department of Chemistry, Valparaiso University, 1710 Chapel Drive, Valparaiso, IN 46383, USA
*
Author for correspondence: Laura Rowe, E-mail: [email protected]
Get access Rights & Permissions [Opens in a new window]

Abstract

Almost all living organisms on Earth utilize the same 20 amino acids to build their millions of different proteins, even though there are hundreds of amino acids naturally occurring on Earth. Although it is likely that both the prebiotic and the current environment of Earth shaped the selection of these 20 proteinogenic amino acids, environmental conditions on extraterrestrial planets and moons are known to be quite different than those on Earth. In particular, the surfaces of planets and moons such as Mars, Europa and Enceladus have a much greater flux of UV and gamma radiation impacting their surface than that of Earth. Thus, if life were to have evolved extraterrestrially, a different lexicon of amino acids may have been selected due to different environmental pressures, such as higher radiation exposure. One fundamental property an amino acid must have in order to be of use to the evolution of life is relative stability. Therefore, we studied the stability of three different proteinogenic amino acids (tyrosine, phenylalanine and tryptophan) as compared with 20 non-proteinogenic amino acids that were structurally similar to the aromatic proteinogenic amino acids, following ultraviolet (UV) light (254, 302, or 365 nm) and gamma-ray irradiation. The degree of degradation of the amino acids was quantified using an ultra-high performance liquid chromatography-mass spectrometer (UPLC-MS). The result showed that many non-proteinogenic amino acids had either equal or increased stability to certain radiation wavelengths as compared with their proteinogenic counterparts, with fluorinated phenylalanine and tryptophan derivatives, in particular, exhibiting enhanced stability as compared with proteinogenic phenylalanine and tryptophan amino acids following gamma and select UV irradiation.

Keywords

Astrobiologyexobiologygamma radiation stabilitynon-proteinogenic amino acidsunnatural amino acidsUV stability
Type
Research Article
Information
International Journal of Astrobiology , Volume 18 , Issue 5 , October 2019 , pp. 426 - 435
Copyright
Copyright © Cambridge University Press 2018 

Access options

Get access to the full version of this content by using one of the access options below. (Log in options will check for institutional or personal access. Content may require purchase if you do not have access.)

References

Alyssa, KC and Ralph, EP (2014) Nature's starships. I. Observed abundances and relative frequencies of amino acids in meteorites. Astrophysical Journal 783, 140.Google Scholar
Barge, LM and White, LM (2017) Experimentally testing hydrothermal vent origin of life on Enceladus and other Icy/ocean worlds. Astrobiology 17, 820–833.Google Scholar
Beaven, GH and Holiday, ER (1952) Ultraviolet absorption spectra of proteins and amino acids. In Anson, ML, Bailey, K and Edsall, JT (eds), Advances in Protein Chemistry, Vol. 7. Elsevier Publishing, pp. 319–386.Google Scholar
Biava, H and Budisa, N (2014) Evolution of fluorinated enzymes: an emerging trend for biocatalyst stabilization. Engineering in Life Sciences 14, 340–351.Google Scholar
Bibring, J-P, Langevin, Y, Poulet, F, Gendrin, A, Gondet, B, Berthé, M, Soufflot, A, Drossart, P, Combes, M, Bellucci, G, Moroz, V, Mangold, N and Schmitt, B, Omega team, t. (2004) Perennial water ice identified in the south polar cap of Mars, Nature 428, 627.Google Scholar
Bonifačić, M, Štefanić, I, Hug, GL, Armstrong, DA and Asmus, K-D (1998) Glycine decarboxylation: the free radical mechanism. Journal of the American Chemical Society 120, 9930–9940.Google Scholar
Boston, PJ, Ivanov, MV and McKay, CP (1992) On the possibility of chemosynthetic ecosystems in subsurface habitats on Mars. Icarus 95, 300–308.Google Scholar
Buer, BC and Marsh, ENG (2012) Fluorine: a new element in protein design. Protein Science 21, 453–462.Google Scholar
Buer, BC, Meagher, JL, Stuckey, JA and Marsh, ENG (2012) Structural basis for the enhanced stability of highly fluorinated proteins. Proceedings of the National Academy of Sciences of the United States of America 109, 4810–4815.Google Scholar
Burton, AS, Stern, JC, Elsila, JE, Glavin, DP and Dworkin, JP (2012) Understanding prebiotic chemistry through the analysis of extraterrestrial amino acids and nucleobases in meteorites. Chemical Society Reviews 41, 5459–5472.Google Scholar
Buxton, GV, Greenstock, CL, Helman, WP and Ross, AB (1988) Critical review of rate constants for reactions of hydrated electrons, hydrogen atoms and hydroxyl radicals (⋅OH/⋅O−in Aqueous Solution. Journal of Physical and Chemical Reference Data 17, 513–886.Google Scholar
Carlson, R, Calvin, W, Dalton, J, Hansen, G, Hudson, R, Johnson, R, McCord, T and Moore, M (2009) Europa's surface composition. In Pappalardo, RT, McKinnon, WB, Khurana, KK and Dotson, R (eds), Europa. University of Arizona Press, pp. 283–327.Google Scholar
Cataldo, F, Ursini, O and Angelini, G (2008) Radioracemization and radiation-induced chiral amplification of chiral terpenes measured by optical rotatory dispersion (ORD) spectroscopy. Radiation Physics and Chemistry 77, 961–967.Google Scholar
Cataldo, F, Angelini, G, Iglesias-Groth, S and Manchado, A (2011 a) Solid state radiolysis of amino acids in an astrochemical perspective. Radiation Physics and Chemistry 80, 57–65.Google Scholar
Cataldo, F, Ragni, P, Iglesias-Groth, S and Manchado, A (2011 b) A detailed analysis of the properties of radiolyzed proteinaceous amino acids. Journal of Radioanalytical and Nuclear Chemistry 287, 903–911.Google Scholar
Cataldo, F, Angelini, G, Hafez, Y and Iglesias-Groth, S (2013 a) Solid state radiolysis of non-proteinaceous amino acids in vacuum: astrochemical implications. Journal of Radioanalytical and Nuclear Chemistry 295, 1235–1243.Google Scholar
Cataldo, F, Iglesias-Groth, S, Angelini, G and Hafez, Y (2013 b) Stability toward high energy radiation of Non-proteinogenic amino acids: implications for the origins of life. Life 3, 449–473.Google Scholar
Cavicchioli, R (2002) Extremophiles and the search for extraterrestrial life. Astrobiology 2, 281–292.Google Scholar
Cherubini, C and Ursini, O (2015) Amino acids chemical stability submitted to solid state irradiation: the case study of leucine, isoleucine and valine. SpringerPlus 4, 541.Google Scholar
Chyba, CF (2000) Energy for microbial life on Europa. Nature 403, 381.Google Scholar
Cleaves, HJ and Miller, SL (1998) Oceanic protection of prebiotic organic compounds from UV radiation. Proceedings of the National Academy of Sciences of the United States of America 95, 7260–7263.Google Scholar
Cooper, J., Sittler, E. Jr, Hartle, R. and Sturner, S. (2008) In European Planetary Science Congress, Vol. 1.Google Scholar
Danchin, A and Sekowska, A (2015) The logic of metabolism. Perspectives in Science 6, 15–26.Google Scholar
Dartnell, LR, Desorgher, L, Ward, J and Coates, A (2007) Modelling the surface and subsurface Martian radiation environment: implications for astrobiology. Geophysical Research Letters 34, 1–6.Google Scholar
Des Marais, DJ, Nuth, JA, Allamandola, LJ, Boss, AP, Farmer, JD, Hoehler, TM, Jakosky, BM, Meadows, VS, Pohorille, A, Runnegar, B and Spormann, AM (2008) The NASA astrobiology roadmap. Astrobiology 8, 715–730.Google Scholar
Edelhoch, H (1967) Spectroscopic determination of tryptophan and tyrosine in proteins*. Biochemistry 6, 1948–1954.Google Scholar
Ehrenfreund, P and Charnley, SB (2000) Organic molecules in the interstellar medium, comets, and meteorites: a voyage from dark clouds to the early earth. Annual Review of Astronomy and Astrophysics 38, 427–483.Google Scholar
Ehrenfreund, P, Bernstein, MP, Dworkin, JP, Sandford, SA and Allamandola, LJ (2001) The photostability of amino acids in space. Astrophysical Journal 550, L95–L99.Google Scholar
Elsila, JE, Aponte, JC, Blackmond, DG, Burton, AS, Dworkin, JP and Glavin, DP (2016) Meteoritic amino acids: diversity in compositions reflects parent body histories. ACS Central Science 2, 370–379.Google Scholar
Fricke, H (1934) The reduction of oxygen to hydrogen peroxide by the irradiation of its aqueous solution with X-rays. Journal of Chemical Physics 2, 556–557.Google Scholar
Griffin, DW (2013) The quest for extraterrestrial life: what about the viruses? Astrobiology 13, 774–783.Google Scholar
Hassler, DM, Zeitlin, C, Wimmer-Schweingruber, RF, Ehresmann, B, Rafkin, S, Eigenbrode, JL, Brinza, DE, Weigle, G, Böttcher, S and Böhm, E (2013) Mars’ surface radiation environment measured with the Mars science laboratory's curiosity rover. Science 343, 1244797-1–1244797-5.Google Scholar
Hays, LE, Graham, HV, Des Marais, DJ, Hausrath, EM, Horgan, B, McCollom, TM, Parenteau, MN, Potter-McIntyre, SL, Williams, AJ and Lynch, KL (2017) Biosignature preservation and detection in Mars analog environments. Astrobiology 17, 363–400.Google Scholar
Henner, WD, Grunberg, SM and Haseltine, WA (1982) Sites and structure of gamma radiation-induced DNA strand breaks. Journal of Biological Chemistry 257, 11750–11754.Google Scholar
Iglesias-Groth, S, Cataldo, F, Ursini, O and Manchado, A (2011) Amino acids in comets and meteorites: stability under gamma radiation and preservation of the enantiomeric excess. Monthly Notices of the Royal Astronomical Society 410, 1447–1453.Google Scholar
Kate, IL, Garry, JR, Peeters, Z, Quinn, R, Foing, B and Ehrenfreund, P (2005) Amino acid photostability on the Martian surface. Meteoritics & Planetary Science 40, 1185–1193.Google Scholar
Kvenvolden, K, Lawless, J, Pering, K, Peterson, E, Flores, J, Ponnamperuma, C, Kaplan, IR and Moore, C (1970) Evidence for extraterrestrial amino-acids and hydrocarbons in the Murchison meteorite. Nature 228, 923–926.Google Scholar
Levy, M, Miller, SL, Brinton, K and Bada, JL (2000) Prebiotic synthesis of adenine and amino acids under Europa-like conditions. Icarus 145, 609–613.Google Scholar
Makwana, KM and Mahalakshmi, R (2015) Implications of aromatic–aromatic interactions: from protein structures to peptide models. Protein Science 24, 1920–1933.Google Scholar
Marion, GM, Fritsen, CH, Eicken, H and Payne, MC (2003) The search for life on Europa: limiting environmental factors, potential habitats, and earth analogues. Astrobiology 3, 785–811.Google Scholar
Marsh, ENG (2014) Fluorinated proteins: from design and synthesis to structure and stability. Accounts of Chemical Research 47, 2878–2886.Google Scholar
McKay, CP, Porco, CC, Altheide, T, Davis, WL and Kral, TA (2008) The possible origin and persistence of life on Enceladus and detection of biomarkers in the plume. Astrobiology 8, 909–919.Google Scholar
Neumann, H, Wang, K, Davis, L, Garcia-Alai, M and Chin, JW (2010) Encoding multiple unnatural amino acids via evolution of a quadruplet-decoding ribosome. Nature 464, 441.Google Scholar
Parkinson, CD, Liang, M-C, Yung, YL and Kirschivnk, JL (2008) Habitability of Enceladus: planetary conditions for life. Origins of Life and Evolution of the Biosphere 38, 355–369.Google Scholar
Peterson, DB, Holian, J and Garrison, WM (1969) Radiation chemistry of the alpha-amino acids. Gamma. Radiolysis of solid cysteine. Journal of Physical Chemistry 73, 1568–1572.Google Scholar
Salih, A, Larkum, A, Cox, G, Kühl, M and Hoegh-Guldberg, O (2000) Fluorescent pigments in corals are photoprotective. Nature 408, 850.Google Scholar
Sarker, PK, Takahashi, J-i, Kawamoto, Y, Obayashi, Y, Kaneko, T and Kobayashi, K (2012) Photostability of isovaline and its precursor 5-ethyl-5-methylhydantoin exposed to simulated space radiations. International Journal of Molecular Sciences 13, 1006.Google Scholar
Schmidt, B, Blankenship, D, Patterson, G and Schenk, P (2011) Active formation of'chaos terrain'over shallow subsurface water on Europa. Nature 479, 502.Google Scholar
Schröder, HF and Meesters, RJW (2005) Stability of fluorinated surfactants in advanced oxidation processes—a follow up of degradation products using flow injection–mass spectrometry, liquid chromatography–mass spectrometry and liquid chromatography–multiple stage mass spectrometry. Journal of Chromatography. A 1082, 110–119.Google Scholar
Schulze-Makuch, D, Irwin, LN and Guan, H (2002) Search parameters for the remote detection of extraterrestrial life. Planetary and Space Science 50, 675–683.Google Scholar
Steel, EL, Davila, A and McKay, CP (2017) Abiotic and biotic formation of amino acids in the Enceladus ocean. Astrobiology 17, 862–875.Google Scholar
Swartz, ME (2005) UPLC™: an introduction and review. Journal of Liquid Chromatography & Related Technologies 28, 1253–1263.Google Scholar
ten Kate, IL (2010) Organics on Mars? Astrobiology 10, 589–603.Google Scholar
Ten Kate, IL, Garry, JR, Peeters, Z, Foing, B and Ehrenfreund, P (2006) The effects of Martian near surface conditions on the photochemistry of amino acids. Planetary and Space Science 54, 296–302.Google Scholar
Tosca, NJ, Knoll, AH and McLennan, SM (2008) Water activity and the challenge for life on early Mars. Science 320, 1204–1207.Google Scholar
Want, EJ, Wilson, ID, Gika, H, Theodoridis, G, Plumb, RS, Shockcor, J, Holmes, E and Nicholson, JK (2010) Global metabolic profiling procedures for urine using UPLC-MS. Nature Protocols 5, 1005.Google Scholar
Waterval, WH, Scheijen, JL, Ortmans-Ploemen, MM, Habets-van der Poel, CD and Bierau, J (2009) Quantitative UPLC-MS/MS analysis of underivatised amino acids in body fluids is a reliable tool for the diagnosis and follow-up of patients with inborn errors of metabolism. Clinica Chimica Acta 407, 36–42.Google Scholar
Weiss, BP, Yung, YL and Nealson, KH (2000) Atmospheric energy for subsurface life on Mars? Proceedings of the National Academy of Sciences 97, 1395–1399.Google Scholar
Xie, J and Schultz, PG (2006) A chemical toolkit for proteins—an expanded genetic code. Nature Reviews. Molecular Cell Biology 7, 775–782.Google Scholar
Xu, RN, Fan, L, Rieser, MJ and El-Shourbagy, TA (2007) Recent advances in high-throughput quantitative bioanalysis by LC–MS/MS. Journal of Pharmaceutical and Biomedical Analysis 44, 342–355.Google Scholar
Supplementary material: File

Rowe et al. supplementary material

Rowe et al. supplementary material 1

Download Rowe et al. supplementary material(File)
File 15.6 MB