Cosmochemical Evolution and the Origins of Life: Proceedings of the Fourth International Conference on the Origin of Life and the First Meeting of the International Society for the Study of the Origin of Life, Barcelona, June 25–28, 1973 Volume II: Contri PDF
Preview Cosmochemical Evolution and the Origins of Life: Proceedings of the Fourth International Conference on the Origin of Life and the First Meeting of the International Society for the Study of the Origin of Life, Barcelona, June 25–28, 1973 Volume II: Contri
COSMOCHEMICAL EVOLUTION AND THE ORIGINS OF LIFE VOLUME II CONTRIBUTED PAPERS COSMOCHEMICAL EVOLUTION AND THE ORIGINS OF LIFE PROCEEDINGS OF THE FOURTH INTERNATIONAL CONFERENCE ON THE ORIGIN OF LIFE AND THE FIRST MEETING OF THE INTERNATIONAL SOCIETY FOR THE STUDY OF THE ORIGIN OF LIFE, BARCELONA, JUNE 25-28, 1973 VOLUME II: CONTRIBUTED PAPERS Edited by J. ORO Departments of Biophysical Sciences and Chemistry, University of Houston, Houston, Texas, and Universidad Autbnoma de Barcelona, Barcelona S. L. MILLER Department of Chemistry, University of California, San Diego, California C. PONNAMPERUMA Laboratory of Chemical Evolution, Department of Chemistry, University of Maryland, College Park, Maryland and R. S. YOUNG Head of Planetary Biology, NASA, Washington, D.C. D. REIDEL PUBLISHING COMPANY DORDRECHT-HOLLAND / BOSTON-U.S.A. Library of Congress Catalog Card Number 74-77967 ISBN-I3: 978-94-010-2284-2 e-ISBN-I3: 978-94-010-2282-8 DOl: 10.1007/978-94-0 10-2282-8 Published by D. Reidel Publishing Company, P.O. Box 17, Dordrecht, Holland Sold and distributed in the U.S.A., Canada and Mexico by D. Reidel Publishing Company, Inc. 306 Dartmouth Street, Boston, Mass. 02116, U.S.A. All Rights Reserved Copyright © 1974 by D. Reidel Publishing Company, Dordrecht, Holland and copyrightholders as specified on appropriate pages within Softcover reprint of the hardcover I 5t edition 1974 No part of this book may be reproduced in any form, by print, photoprint, microfilm, or any other means, without written permission from the publisher T ABLE OF CONTENTS PART I/ORGANIC COSMOCHEMISTRY JAMES G. LAWLESS and ETT A PETERSON / Amino Acids in Carbonaceous Chondrites 3 HANS E. SUESS / Remarks on the Chemical Conditions on the Surface of the Primitive Earth and the Probability of the Evolution of life 9 MIKIO SHIMIZU / Molten Earth and the Origin of Prebiological Molecules 15 DUWAYNE M. ANDERSON and AMOS BANIN / Soil and Water and Its Rela- tionship to the Origin of Life 23 RICHARD Y. MORIT A / Microbial Contributions to the Evolution of the 'Steady State' Carbon Dioxide System 37 A. s. LOPUCHIN / Structure of Biogenic Origin from Early Precamoriam Rocks of Euro-Asia 45 PART II / ABIOTIC ORGANIC SYNTHESIS SHIN-SHYONG TSENG and SHER WOOD CHANG (Photochemical Synthesis of Simple Organic Free Radicals on Simulated Planetary Surfaces - an ESR Study 61 s. YUASA and M. ISHIGAMI / High Frequency Discharge Experiment 75 G. TOUPANCE,F. RAULIN, andR. BUVET /FormationofPrebiochemicaICom pounds in Models of the Primitive Earth's Atmosphere. I: CH -NH and 4 3 CH4 - N 2 Atmospheres 83 F. RAULIN and G. TOUPANCE / Formation of Preb iochemical Compounds in Models of the Primitive Earth's Atmosphere. II:CH -H S Atmospheres 91 4 2 w. K. PARK, A. R. HOCHSTIM, and c. PONNAMPERUMA / Organic Synthesis by Quench Reactions 99 A. BAR-NUN / Shock Synthesis of Amino Acids II 109 G. H. LOEW and S. CHANG / Quantum Chemical Study of the Thermodynamics, Kinetics of Formation and Bonding ofH CN: Relevance to Prebiotic Chem- 2 istry 117 MOHINDRA s. CHADHA, PETER M. MOL TON, and CYRIL PONN AMPER UMA / Aminonitriles: Possible Role in Chemical Evolution 127 PART III / ABIOTIC ORGANIC SYNTHESIS AND INTERACTIONS: POLYMERS HARUHIKO NODA, HIROSHI MIZUTANI, and HIROYUKI OKIHANA / Macromolecules and the Origin of Life 139 VI TABLE OF CONTENTS SALVATORE ANDINI, ETTORE BENEDETTI, LUCIANO FERRARA, LIVIO PAOLILLO, and PIERO ANDREA TEMUSSI / NMR Studies of Prebiotic Polypeptides 147 CLIFFORD N. MA TTHEWS / The Origin of Proteins: Heteropolypeptides from Hydrogen Cyanide and Water 155 ALAN W. SCHWARTZ, M. VAN DER VEEN, T. BISSELING, and G. J. F. CHIT TENDEN / Prebiotic Nucleotide Synthesis-Demonstration of a Geologically Plausible Pathway 163 M. HALMANN / Models of Preb iological Phosphorylation 169 ELISABETH ET AIX and RENE BUVET / Conditions of Occurrence for Pri- meval Processes of Transphosphorylations 175 PART IV / STRUCTURAL AND THERMODYNAMIC CONSIDERATIONS ON THE ORIGIN OF LIFE WILLIAM A. BONNER and JOSE J. FLORES / Experiments on the Origins ofOp- tical Activity 187 K. D. HAEGELE, P. Y. HOWARD, and w. PARR / A Technique for the Determi- nation of Enantiomeric Amino Acids in Biological Samples 195 DUANE L. ROHLFING / Coacervate-Like Microspheres from Lysine-Rich Proteinoid 203 P. DECKER / Evolution in Bioids: Hypercompetitivity as a Source of Bistability and a Possible Role of Metal Complexes as Prenucleoprotic Mediators of Molecular Asymmetry 211 MASAMI HASEGAWA and TAKA-AKI YANO / Entropy of the Genetic In- formation and Evolution 219 c. A. BOGDANSKI/Physical Foundations of the Probability of Biogenesis 229 M. MCCABE / Some Physical Parameters Controlling Cell Size During the Evo- lution of the Procaryons 239 PART V / EARLY BIOCHEMICAL EVOLUTION E. BRODA / The Beginning of Photosynthesis 247 N. V. KARAPETY AN / Evolution of Photo systems of Photosynthetic Organisms 253 v. M. KUTYURIN / Evolution of Oxygen by Plants in Relation to Biosphere Evolution 257 A. G. CAIRNS-SMITH / Ambiguity in the Interpretation of Abiotic Syntheses 265 VLADIMIR NOV A.K and VLASTIMIL LIEBL / On the Question of the Origin and Evolution of the Genetic System 269 JAMES C. LACEY, JR., ARTHUR L. WEBER, and WILLIAM E. WHITE, JR. / A Model for the Coevolution of the Genetic Code and the Process of Protein Synthesis: Review and Assessment 273 TABLE OF CONTENTS VII PART VI/MISCELLANEOUS PAPERS KONG-YI HONG, JANE-HUEY HONG, and RALPH S. BECKER / Hot Hy drogen Atoms: Initiators of Reactions of Interest in Interstellar Chemistry and Evolution 287 s. YU ASA and 1. ORO / Role of Weak Bases on the Prebiotic Formation of Het- erocyclic Compounds 295 E. STEPHEN-SHERWOOD, D. G. ODOM, and J. ORO / The Prebiotic Synthesis of Deoxythymidine Oligonucleotides 301 L. E. ORGEL / A Possible Step in the Origin of the Genetic Code 309 A. GINER-SOROLLA and A. BENDICH / The Emergence of Carcinogens During the Evolution of Living Systems 315 INDEX OF SUBJECTS 325 PART I ORGANIC COSMOCHEMISTRY AMINO ACIDS IN CARBONACEOUS CHONDRITES JAMES G. LAWLESS and ETTA PETERSON Ames Research Center, NASA, Planetary Biology Division, Moffett Field, Calif. 94035, U.S.A. Abstract. For almost 20 years laboratory experiments have advanced the concepts of chemical evolution, particularly with regard to formation of the amino acids. What has been generally lacking is concrete natural evidence for this chemical evolution hypothesis. The recent development of sophisticated analytical techniques and availability of carbonaceous chondrites with a minimum of terrestrial contamination has resulted in the identification of amino acids which provide strong evidence for a natural extraterrestrial chemical synthesis. Since the initial find in the Murchison meteorite (a type II carbonaceous chondrite) of both protein and nonprotein amino acids and amino acids with nearly equal abundances of D and L isomers, further studies have been carried out. These studies have revealed the presence of at least 35 amino acids; the population consists of a wide variety of linear, cyclic and polyfunctional amino acids which shows a trend of decreasing concentration with increasing carbon number. Investigations of the Murray meteorite (a type II carbonaceous chondrite) has produced similar results, but studies of the Orgueil meteorite (a type I carbomiceous chondrite) show only a limited suite of amino acids, some of which appear to be indigenous while others appear to be terrestrial contaminants. A sample of the Murchison meteorite was extracted with D 0 and in addition to 'free' amino acids, showing no deuterium incorpora 2 tion, some amino acids showed the presence of deuterium suggesting either a 'precursor(s)' or hydrogen deuterium exchange which require(s) formation of carbon-hydrogen bonds. 1. Introduction One of the most important classes of compounds in the scheme of chemical evolu tion is the amino acids. Since the initial identification of these compounds as products of an electrical discharge in an atmosphere of methane, ammonia, and water, many investigators have contributed to an extensive body of literature concerning their production in simulated prebiotic experiments. This abundance of data provides an impressive experimental base for the hypothesis of chemical evolution. Since the laws of chemistry are believed to be universal, there should be natural evidence for the chemical evolutionary process. Meteorites, particularly carbonaceous chon drites, appear to provide such evidence. Recently, Kvenvolden et al. (1970) identified amino acids - as well as other compounds - in the Murchison meteorite, a type II carbonaceous chondrite. The suite of amino acids found included protein and nonprotein amino acids, with many of these amino acids having nearly equal amounts of both the D and the L isomers. Subsequent investigations of the Murchison and other meteorites (Kvenvolden et al., 1971; Cronin and Moore, 1971; Oro et al., 1971a; Lawless et at., 1971; Oro et al., 1971b; Lawless et al., 1972) have substan tiated this finding and provided the strongest evidence to date for the indigenous nature of complex organic molecules in extraterrestrial samples. The recent develop ment of sophisticated analytical techniques, particularly the combined gas chromato graph-mass spectrometer (GC-MS), has been instrumental in the success of these investigations. This paper reports on the use of GC-MS to characterize further the amino acids found in extracts of the Murchison meteorite. 4 JAMES G. LAWLESS AND ETTA PETERSON 2. Experimental Two separate samples of the Murchison meteorite were analyzed. The first 5.1 g sample was refluxed with deuterated water (D 20) for 20 hr. The D 20 extract was charged on a Dowex 50 (H +) ion exchange column and eluted with H 0 and 2N 2 NH 0H. A second 10 g sample of pulverized meteorite was refluxed with H 0 for 4 2 20 hr. The H 0 extract was evaporated to dryness and refluxed with 6N HCI for 2 20 hr. The hydrolyzate was evaporated to dryness, redissolved in H 0, and charged 2 on a Dowex 50 (H +) ion exchange column. The column was successively eluted with HP and 2NNHpH. In each case the NH 0H eluate was evaporated to 4 dryness, and the N-trifluoroacetyl-D-2-butyl ester derivatives of the amino acids were prepared (Pollock et at., 1965; Pollock and Oyama, 1966). These compounds were analyzed by gas chromatography (Perkin-Elmer 900) using a flame ionization detector and a 150 ft x 0.02 in wall coated (UCON 75-H-90000) capillary column. The column was programmed from 100° to 150°C at 1°C min Procedural blanks -1. showed no amino acids. The same column and gas chromatographic conditions were used in the GC-MS analysis where the gas chromatograph was interfaced to a CEC 21-491 mass spec trometer through a membrane separator. As each compound eluted from the gas chromatograph and passed into the mass spectrometer, its mass spectrum was ob tained using 70 eV electrons by taking successive scans at 4 s per decade. The co variant mass spectral peaks were then plotted and the identity of the compound determined. This GC-MS system is capable of identifying as little as 20 x 10 g -9 of the N-trifluoroacetyl-D-2-butyl ester derivative of an amino acid injected onto the gas chromatographic column. 3. Results and Discussion Cronin and Moore (1971) observed a marked increase in the concentration of most of the amino acids as a result of acid hydrolysis of the Murchison meteorite aqueous extract. They pointed out that the state of the amino acids prior to extraction and the chemical reactions which they may undergo during extraction were not known. In order to understand further what might be happening during the extraction procedure, a sample of the Murchison meteorite was extracted with D 0 and the 2 resulting amino acids derivatized and analyzed by GC-MS. If carbon-hydrogen bond formation occurs during extraction and involves the extraction solvent, use of D 20 would result in carbon-deuterium bond formation which could be detected in the mass spectra of the derivatized amino acids. The results of this experiment are sum marized by the mass spectral data presented in Table I. First, it should be noted that with the exception of p-aminoisobutyric acid, all of the amino acids which were found in previous studies of the Murchison meteorite (Kvenvolden et al., 1970; Kvenvolden et al., 1971; Oro et at., 1971a; Cronin and Moore, 1971) and the Murray meteorite (Cronin and Moore, 1971; Lawless et at., 1971) have been identified in AMINO ACIDS IN CARBONACEOUS CHONDRITES 5 TABLE I Major fragment ions of the amino acids found in the Murchison meteorite D 0 extractt 2 .. .. .• 1~t"0: <c '~~;d .~"~~& i6"ro,' t ' ~."~.-"""-- J~~ ~,~~h ~I~i c]th~~~2~ .!~ .N~. .!~ ..~~. i~:.\:!l .!~~ .2.N.:g1 ~,!,.,.~~~~~~ ..'~~"~"\"-! :].~\":!l :i~~~;~Ji :~~"&;g~"J' " ~~ 100 8 6 102 3 1 2 103 3 4 3 104 3 6 110 13 112 10 17 113 5 11ft 11 9 15 12 115 14 116 8 7 120 10 27 12 126 6 11 7 48 40 100 75 17 21 4 24 31 19 127 2 3 3 34 16 87 100 45 44 2 5 128 10 8 14 52 100 100 4 129 5 13 46 49 2 130 5 2 3 3 138 10 10 139 1 18 16 11 42 21 140 3 3 100 100 64 38 96 8 11 16 27 141 3 87 99 19 24 13 4 8 1 1 142 20 42 2 4 3 5 4 4 143 2 11 25 25 144 100 100 145 41 47 146 3 3 147 1 1 152 2 3 6 6 2 1 2 51 153 25 8 5 10 12 19 6 2 2 1 10 33 154 100 34 100 100 100 18 15 73 45 10 8 29 17 155 16 3 18 78 65 12 17 15 42 31 20 7 156 2 19 18 7 5 12 48 42 157 3 2 3 4 1 3 3 164 2 165 166 9 7 3 2 4 5 11 9 110~ 167 4 3 1 2 5 7 6 22 168 100 100 21 29 100 100 100 3 169 12 56 8 16 95 21 77 1 170 12 2 4 24 4 25 171 10 14 3 172 173 180 2 3 4 5 100 6 73 181 23 5 14 16 52 182 14 14 15 15 100 2 100 17 183 2 2 5 5 33 14 184 12 5 16 4 70 185 1 2 13 6 7 8 75 186 14 12 14 187 5 10 188 3 194 1 3 8 6 195 2 1 1 196 5 14 18 197 1 3 9 198 100 199 11 30 62 200 17 9 22 201 4 207 2 208 6 209 1 211 4 212 1 11~~ 213 214 20 225 17 226 100 227 I 33 228 16 I tEach mass spectrum is normalized to the most abundant ion above role 100. *D ata from successive scans of the GC peak showing partial chromatographic separation of nondeuterated and deuterated species. ** A synthesized sample of alanine with approximately 75% D4 shows no mass spectral differences between direct probe and GC-MS methods of sample introduction.
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