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On the Origin of Single Chirality of Amino Acids and Sugars in Biogenesis

Accounts of Chemical Research2012Vol. 45(12), pp. 2045–2054

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Abstract

The process of delineating the origins of the chemistry of life starts with the consideration of the molecules that might have existed on prebiotic earth and extends to the discussion of potential mechanisms for assembly of these molecules into informational polymers capable of self-replication and transmittance of genetic information. At some point along this pathway, the property of single chirality emerges as the hallmark of the amino acids and sugars present in biological molecules. In the 20th century, researchers developed abstract mathematical theses for the origin of biomolecular homochirality from a presumably racemic collection of prebiotic molecules. Before the end of that century, experimental findings corroborated a number of basic features of these theoretical models, but these studies involved chemical systems without direct prebiotic relevance. Currently researchers are examining prebiotically plausible conditions that couple chemical and physical processes leading to single chirality of sugars and amino acids with subsequent chemical reactions that enhance molecular complexity. While these studies have been conducted for the most part in the context of the RNA World hypothesis, the experimental findings remain relevant to a "metabolism first" model for the origin of life. To many chemists interested in chembiogenesis, the synthesis of activated pyrimidine ribonucleotides under potentially prebiotic conditions by Sutherland's group provided a landmark demonstration of what Eschenmoser has described as "an intrinsic structural propinquity" between certain elementary chemical structures and modern biological molecules. Even while some synthetic issues for plausible prebiotic construction of RNA remain unsolved, our work has focused on coupling these synthetic advances with concepts for the evolution of biomlolecular homochirality. Drawing on our own findings as well as those from others, we present an intriguing "chicken or egg" scenario for the emergence of single chirality of sugars and amino acids. Our work incorporates both chemical and physical phenomena that allow for the amplification of a small initial imbalance of either sugars by amino acids or amino acid by sugars, suggesting that an enantioenriched chiral pool of one type of molecule could lead to a similarly enantioenriched pool of the other.

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Abstract

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