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Amino Acids and the Asymmetry of Life; Springer, 2008.Pdf Amino Acids and the Asymmetry of Life Advances in Astrobiology and Biogeophysics springer.com This series aims to report new developments in research and teaching in the inter- disciplinary fields of astrobiology and biogeophysics. This encompasses all aspects of research into the origins of life – from the creation of matter to the emergence of complex life forms – and the study of both structure and evolution of planetary ecosystems under a given set of astro- and geophysical parameters. The methods con- sidered can be of theoretical, computational, experimental and observational nature. Preference will be given to proposals where the manuscript puts particular emphasis on the overall readability in view of the broad spectrum of scientific backgrounds involved in astrobiology and biogeophysics. The type of material considered for publication includes: • Topical monographs • Lectures on a new field, or presenting a new angle on a classical field • Suitably edited research reports • Compilations of selected papers from meetings that are devoted to specific topics The timeliness of a manuscript is more important than its form which may be un- finished or tentative. Publication in this new series is thus intended as a service to the international scientific community in that the publisher, Springer-Verlag, offers global promotion and distribution of documents which otherwise have a restricted readership. Once published and copyrighted, they can be documented in the scientific literature. Series Editors: Dr. André Brack Dr. Christopher P. McKay Centre de Biophysique Moléculaire NASA Ames Research Center CNRS, Rue Charles Sadron Moffet Field 45071 Orléans, Cedex 2, France CA 94035,USA [email protected] Dr. Gerda Horneck Prof. Dr. H. Stan-Lotter DLR, FF-ME Institut für Genetik Radiation Biology und Allgemeine Biologie Linder Höhe Universität Salzburg 51147 Köln, Germany Hellbrunnerstr. 34 [email protected] 5020 Salzburg, Austria Uwe Meierhenrich Amino Acids and the Asymmetry of Life Caught in the Act of Formation With a Foreword by Henri B. Kagan 123 Prof. Dr. Uwe Meierhenrich Universite´ de Nice-Sophia Antipolis Faculte´ des Sciences CNRS UMR 6001 Parc Valrose 06108 Nice France [email protected] ISBN: 978-3-540-76885-2 e-ISBN: 978-3-540-76886-9 Library of Congress Control Number: 2008930865 c 2008 Springer-Verlag Berlin Heidelberg This work is subject to copyright. All rights are reserved, whether the whole or part of the material is concerned, specifically the rights of translation, reprinting, reuse of illustrations, recitation, broadcasting, reproduction on microfilm or in any other way, and storage in data banks. Duplication of this publication or parts thereof is permitted only under the provisions of the German Copyright Law of September 9, 1965, in its current version, and permission for use must always be obtained from Springer. Violations are liable to prosecution under the German Copyright Law. The use of general descriptive names, registered names, trademarks, etc. in this publication does not imply, even in the absence of a specific statement, that such names are exempt from the relevant protective laws and regulations and therefore free for general use. Cover design: eStudio Calamar S.L. Printed on acid-free paper 987654321 springer.com for Eva Foreword A book on amino acids in the context of the origin of life and life’s homochirality is unusual. Professor Meierhenrich has written a very detailed scenario on the at- tempts of scientists to propose hypotheses taking into account the stereochemical information given by the analysis of organic molecules. One key tool refers to the famous statement of Louis Pasteur in his lectures: “Optical activity is a signature of life”. The author presents many facets of the chemical and physical processes involved on earth or in space and he enters into a fascinating area of ongoing scientific debate. At times the diversity of the topics involved might be demanding for undergraduates or newcomers to the field, but the book, while challenging, illuminates the way science is progressing among a wide diversity of techniques, scientific areas, and hypotheses. When I started preparing my Ph.D. thesis at the College` de France in Paris under the supervision of Dr. Jean Jacques, I was attracted by the possibility of deducing the shape of molecules, including their absolute configuration, from experimental data, either spectroscopic or chemical. Organic chemistry remained strongly con- nected to pharmaceutical chemistry, where many compounds of biological interest are asymmetric and optically active. The manipulation of molecular models as Drei- ding models (there were no computers at that time) allowed for analysing the three- dimensional behaviour of many rigid or mobile structures. Conformational analysis of cyclohexane and polycyclic systems such as steroids have been recently rational- ized by D. H. R Barton and O. Hassel (Nobel prize winners in 1969). The prediction of the steric course of reactions that create a new asymmetric center became possible and was based on simple concepts. After my Ph.D., I was involved in a fruitful col- laboration with Prof. Alain Horeau, Head of the Organic Chemistry Laboratory at the College` de France. He proposed a chemical method to establish the absolute con- figuration of an asymmetric center of secondary alcohols RCHR(R’)OH as well as deuterated primary alcohols RCHD(R)OH. I was associated with the latest develop- ments of the Horeau’s method. Later, I started, always in association with A. Horeau, to approach the difficult problem of efficiently creating an asymmetric center in an achiral molecule (asymmetric synthesis). For that purpose, we used chiral auxil- iaries temporarily connected to a substrate or a reagent. Especially successful was an asymmetric synthesis that provided almost enantiomerically pure aspartic acid. vii viii Foreword When I became scientifically independent, I launched two completely different projects simultaneously in Orsay. One was the exploration of asymmetric catalysis using chiral transition metals. The other was to revisit the old question of the use of a chiral physical agent such as circularly polarized light (CPL), already suggested by Pasteur and Le Bel in 1860–1874. In asymmetric catalysis, we made important dis- coveries in the 1970s by devising chiral ligands (C2-symmetric chiral diphosphines) for rhodium complexes. These new catalysts allowed preparation of α-amino acids by asymmetric hydrogenation with up to 80% enantiomeric excess (e.e.), values which were the highest at that time. Nowadays, some enantioselective catalysts are used in industry to prepare chiral compounds with 99% e.e. Our second project was more in line with the topic of the present book. The pres- ence of circularly polarized light, a chiral agent, has been suggested to be present when the prebiotic soup started to produce biomolecules. Pasteur, Le Bel, van’t Hoff, Cotton, Kuhn, and many others considered this possibility seriously, but it was W. Kuhn, who, in 1929–1930, first performed a partial asymmetric photolysis of a racemic compound (N,N-dimethyl α-azidopropionamide). The recovered ma- terial was optically active, although of very small e.e. This case of kinetic resolution was not followed by other examples until 1974, when we clearly showed that kinetic resolution of camphor can be carried out with CPL and afforded recovered camphor with 20 % e.e. at high conversion. The key factor for a successful experiment is to select a compound with a good g factor (g = Δε/ε). Later several groups estab- lished that CPL can also be used to perform similar experiments on amino acids. In 1971, we described the first example of an asymmetric synthesis by using an achiral substrate and CPL. A photolytic cyclization gave rise to hexahelicene, which was slightly enriched in one enantiomer. This was easy to measure with a polarimeter because hexahelicene has a huge specific rotation. With regard to the question of whether CPL is able to produce optically active compounds, we learned that the answer is “yes”. But what is its prebiotic significance? This question still remains unanswered. We were also involved in a third project that may be of interest for prebiotic chemistry: the amplification of a small enantiomeric excess by catalytic or stoichio- metric methods. In fact, we showed in 1986 that it is possible to use an enantioim- pure catalyst to create a product of higher enantiomeric excess than the one of the catalyst. This effect was named the “nonlinear effect” and it can be useful in auto- catalytic reactions. In 2007, we established experimentally, as proposed by I. Ugi in 1977, that some racemic reagents can increase the e.e. of partially resolved samples thanks to a selective destruction of some racemic content in the samples. The present book discusses many ways to initiate or develop optical activity from achiral or racemic materials. The outlined space exploration and the study of chi- ral molecules are certainly of great interest to better understand the origin of ho- mochirality of biological systems. The underlying problem, however, may remain unsolved for a long period of time, if not forever. The scientific subject is intel- lectually appealing, and it has great potential for attracting young people towards chemistry as well as the physical and natural sciences. Orsay, France Henri B. Kagan May 2008 “Now, if you’ll only attend, Kitty, and not talk so much, I’ll tell you all my ideas about Looking-glass House. First, there’s the room you can see through the glass – that’s just the same as our drawing room, only the things go the other way. I can see all of it when I get upon a chair – all but the bit behind the fireplace. Oh! I do so wish I could see that bit! I want so much to know whether they’ve a fire in the winter: you never can tell, you know, unless our fire smokes, and then smoke comes up in that room too – but that may be only pretence, just to make it look as if they had a fire.
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