The two enantiomers of the amino acid serine represent the starting point in a series of chemical events that may have led, via the serine octamer, to chiral accumulation and ultimately to the birth of homochiral life. In the Frontispiece, the blue water represents the primordial matrix, serine stirs the terrestrial pot, and by still puzzling processes, life—represented by the acorn—swirls out from the prebiotic system. The picture was created by Zheng Ouyang.
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Review
Serine Octamers: Cluster Formation, Reactions, and Implications for Biomolecule Homochirality†
Article first published online: 11 JAN 2006
DOI: 10.1002/anie.200501328
Copyright © 2006 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Additional Information
How to Cite
Nanita, S. C. and Cooks, R. G. (2006), Serine Octamers: Cluster Formation, Reactions, and Implications for Biomolecule Homochirality. Angewandte Chemie International Edition, 45: 554–569. doi: 10.1002/anie.200501328
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Publication History
- Issue published online: 11 JAN 2006
- Article first published online: 11 JAN 2006
- Manuscript Received: 16 APR 2005
- Abstract
- Article
- References
- Cited By
Keywords:
- chemical evolution;
- cluster compounds;
- homochirality;
- mass spectrometry;
- serine
Graphical Abstract
A remarkable example of magic-number clustering and chiral recognition in molecular aggregates is shown by serine octamers, which partly explains two essential steps in the origin of homochirality: enantiomeric enrichment and chiral transfer (see picture). Extensive investigations over the past five years have revealed many facts about the structure(s), chemistry, and mechanism of formation of serine octamers.
Abstract
The emergence of homochirality continues to be one of the most challenging topics associated with the origin of life. One possible scenario is that aggregates of amino acids might have been involved in a sequence of chemical events that led to chiral biomolecules in self-replicating systems, that is, to homochirogenesis. Serine is the amino acid of principal interest, since it forms “magic-number” ionic clusters composed of eight amino acid units, and the clusters have a remarkable preference for homochirality. These serine octamer clusters (Ser8) can be generated under simulated prebiotic conditions and react selectively with other biomolecules. These observations led to the hypothesis that serine reactions were responsible for the first chiral selection in nature which was then passed through chemical reactions to other amino acids, saccharides, and peptides. This Review evaluates the chemistry of Ser8 clusters and the experimental evidence that supports their possible role in homochirogenesis.