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Origins of Life and Evolution of Biospheres

, Volume 49, Issue 3, pp 163–185 | Cite as

Interactions of Amino Acids and Aminoxazole Derivatives: Cocrystal Formation and Prebiotic Implications Enabled by Computational Analysis

  • Nieves LavadoEmail author
  • Juan García de la ConcepciónEmail author
  • Reyes Babiano
  • Pedro Cintas
  • Mark E. Light
Theoretical Paper

Abstract

In line with the postulated intermediacy of aminoxazoles derived from small sugars toward the direct assembly of nucleoside precursors, we show here a potential prebiotic scenario where aminoxazolines might have also played further roles as complexing and/or sequestering agents of other primeval blocks, namely amino acids. To this end, a bis-aminoxazoline derivative, generated from dihydroxyacetone and cyanamide, gives rise to stable co-crystal forms with dicarboxylic amino acids (Asp and Glu), while ionic interactions owing to proton transfer are inferred from spectroscopic data in aqueous solution. The structure of a 1:2 aminoxazoline: aspartic acid complex, discussed in detail, was elucidated by X-ray diffractometry. Optimized geometries of such ionic structures with bulk aqueous solvation were assessed by DFT calculations, which disclose preferential arrangements that validate the experimental data. Peripherally, we were able to detect in a few cases amino acid dimerization (i.e. dipeptide formation) after prolonged incubation with the bis-aminoxazole derivative. A mechanistic simulation aided by computation provides some predictive conclusions for future explorations and catalytic design.

Keywords

Prebiotic chemistry Amino acids Aminoxazole chemistry Reaction mechanism Dipeptide 

Notes

Acknowledgements

This work was supported by Junta de Extremadura and Fondo Europeo de Desarrollo Regional (Grants IB16167 and GR18015). We also gratefully acknowledge the Cénits/COMPUTAEX Foundation for providing computing time on the LUSITANIA Supercomputer.

Supplementary material

11084_2019_9582_MOESM1_ESM.docx (3.1 mb)
ESM 1 (DOCX 3152 kb)

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Copyright information

© Springer Nature B.V. 2019

Authors and Affiliations

  1. 1.Departamento de Química Orgánica e Inorgánica, Facultad de Ciencias-UEXBadajozSpain
  2. 2.Department of Chemistry, Faculty of Natural and Environmental SciencesUniversity of SouthamptonSouthamptonUK

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