This book presents the fascinating formation of the first simple bioorganic molecules and describes the hidden aspects of chiral compounds, which raise questions on the molecular beginnings of life. The occurrences of extraterrestrial, non-standard amino acids in meteorites are dealt with in detail, as well as their subsequent transfer to proteinogenic amino acids. The concept of asymmetric organo-catalysis for the synthesis of carbohydrates and ribonucleosides are considered. The notion of a single amino acid that functions as an enzyme is developed. Attempts to simulate ancient world scenarios are critically reviewed. There is a special focus on ribozymes and the resulting RNA world. Combinations of different world scenarios are discussed in view of an on-going evolution. The currently most plausible hypotheses and visions of ancient world scenarios that led to today's DNA world are also provided. Included is a pre-cellular world of viruses that is presented for the first time.

Part I. Physico-chemical Principles

1. Introduction

2. Formation of primordial bioorganic molecules

3. Hidden Aspects of Chirality

4. RNAs and their constituents

5. Proteins and their constituents

6. Membranes

7. Compounds Required for Life

Part II. Scenarios of Ancient Worlds

8. The RNA World Involves RNA as a First Genetic System

9. Peptide and Protein World

10. Combinations of the RNA with the peptide world

11. The Precellular World of Viruses

12. Combinations of Different Worlds

13. The Iron Sulfide World of Proto-Metabolism

1;Chirality and Life;3 1.1;Preface and Acknowledgments;5 1.2;Contents;7 1.3;Abbreviations;9 1.4;Part I: Physicochemical Principles;11 1.4.1;Chapter 1: Introduction;12 1.4.2;Chapter 2: Formation of Primordial Bioorganic Molecules;15 1.4.3;Chapter 3: Hidden Aspects of Chirality;16 1.4.3.1;3.1 Asymmetric UV Photolysis of a Racemic Amino Acid;17 1.4.3.2;3.2 Occurrences of a-Methyl Amino Acids in Meteorites;18 1.4.3.3;3.3 Partial Transfer of Enantiomeric Excess of a-Alkyl Amino Acids to Standard Amino Acids;20 1.4.3.4;3.4 Amplification of Enantiomeric Concentrations Without Catalysis;20 1.4.3.5;3.5 Thermodynamic Control of Asymmetric Amplification in Amino Acid Catalysis;20 1.4.3.6;3.6 Asymmetric Organocatalysis: Special Importance of Chiral Proline;21 1.4.3.7;3.7 Amplification of Ribonucleosides;22 1.4.3.8;3.8 The Soai Reaction;23 1.4.3.9;3.9 Spontaneous Formation of Chiral Crystals of Cytosine During Mechanical Stirring;25 1.4.3.10;3.10 The Butlerov or Formose Reaction;26 1.4.3.11;3.11 Conclusions from the Aspects of Chirality;27 1.4.4;Chapter 4: RNAs and Their Constituents;29 1.4.4.1;4.1 Nucleobases;29 1.4.4.2;4.2 Carbohydrates;29 1.4.4.3;4.3 Phosphodiester;30 1.4.4.4;4.4 Classes of RNA;31 1.4.4.4.1;4.4.1 Transfer RNA;31 1.4.4.4.2;4.4.2 Ribosomal RNA;32 1.4.4.4.3;4.4.3 Messenger RNA;32 1.4.4.4.4;4.4.4 Micro and Small RNAs;33 1.4.4.4.5;4.4.5 RNA Modifications;33 1.4.5;Chapter 5: Proteins and Their Constituents;34 1.4.5.1;5.1 Amino Acids;34 1.4.5.2;5.2 Posttranslational Modification;37 1.4.5.3;5.3 Protein Structural Motifs: a-Helix, beta-Sheet, beta-Turns;37 1.4.5.4;5.4 Protein Domains;37 1.4.6;Chapter 6: Membranes;38 1.4.6.1;6.1 Long Chain Fatty Acids Esterified with Phosphoryl Groups: Lipid Bilayer of Bacterial Membranes;38 1.4.6.2;6.2 Prenyl Chains Linked to Di-Isoprene Phosphate via Ether Bridges: Lipid Mono- and Bilayers of Archaeal Membranes;38 1.4.7;Chapter 7: Compounds Required for Life;43 1.4.7.1;7.1 Water;43 1.4.7.2;7.2 Coenzymes;43 1.5;Part II: Scenarios of Ancient Worlds;46 1.5.1;Chapter 8: The RNA World: RNA as a First Genetic System;47 1.5.2;Chapter 9: Peptide and Protein Worlds;49 1.5.3;Chapter 10: Combination of Ribozymes with Peptides: The Evolving RNA Peptide World;50 1.5.4;Chapter 11: The Precellular World of Viruses;53 1.5.5;Chapter 12: Combinations of Different Worlds;55 1.5.6;Chapter 13: The Iron Sulfide World of Protometabolism;56 1.5.7;Chapter 14: The Evolution of the Genetic Code;60 1.6;References;62 1.7;Subject Index;64