Journal of Molecular Evolution

, Volume 70, Issue 6, pp 572–582 | Cite as

Amino Acid Homochirality may be Linked to the Origin of Phosphate-Based Life

  • Da Xiong Han
  • Hai Yan Wang
  • Zhi Liang Ji
  • An Fu Hu
  • Yu Fen Zhao


Phosphorylation has to have been one of the key events in prebiotic evolution on earth. In this article, the emergence of phosphoryl amino acid 5′-nucleosides having a P–N bond is described as a model of the origin of amino acid homochirality and Genetic Code. It is proposed that the intramolecular interaction between the nucleotide base and the amino acid side-chain influences the stability of particular amino acid 5′-nucleotides, and the interaction also selects for the chirality of amino acids. The differences between l- and d-conformation energies (ΔEconf) are evaluated by DFT methods at the B3LYP/6-31G(d) level. Although, as expected, these ΔEconf values are not large, they do give differences in energy that can distinguish the chirality of amino acids. Based on our calculations, the chiral selection of the earliest amino acids for l-enantiomers seems to be determined by a clear stereochemical/physicochemical relationship. As later amino acids developed from the earliest amino acids, we deduce that the chirality of these late amino acids was inherited from that of the early amino acids. This idea reaches far back into evolution, and we hope that it will guide further experiments in this area.


Homochirality Genetic codes Phosphate Origin of life Chiral selection 



We thank Professor G. Michael Blackburn for useful discussions. This study was supported by the National Science Foundation of China (Grant No. 40976050 and Grant No. 40706043) and the 908 Project Foundation of State Oceanic Administration of China (FJ 908-02-03-05).


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Copyright information

© Springer Science+Business Media, LLC 2010

Authors and Affiliations

  • Da Xiong Han
    • 1
  • Hai Yan Wang
    • 2
  • Zhi Liang Ji
    • 3
  • An Fu Hu
    • 3
  • Yu Fen Zhao
    • 3
  1. 1.Department of PharmacyMedical College of Xiamen UniversityXiamenChina
  2. 2.The Third Institute of OceanographyState Oceanic Administration of ChinaXiamenChina
  3. 3.The Key Laboratory for Chemical Biology of Fujian Province, College of Chemistry and Chemical EngineeringXiamen UniversityXiamenChina

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