Interactions of Amino Acids and Aminoxazole Derivatives: Cocrystal Formation and Prebiotic Implications Enabled by Computational Analysis
| Autor: | Pedro Cintas, Nieves Lavado, Mark E. Light, Juan García de la Concepción, Reyes Babiano |
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| Rok vydání: | 2019 |
| Předmět: |
chemistry.chemical_classification
Aqueous solution Dipeptide Origin of Life Solvation Computational Biology Ionic bonding General Medicine 01 natural sciences Cocrystal Amino acid chemistry.chemical_compound Computational Chemistry chemistry Space and Planetary Science Computational chemistry 0103 physical sciences Aspartic acid Cyanamide Amino Acids Oxazoles 010303 astronomy & astrophysics Ecology Evolution Behavior and Systematics |
| Zdroj: | Origins of Life and Evolution of Biospheres. 49:163-185 |
| ISSN: | 1573-0875 0169-6149 |
| DOI: | 10.1007/s11084-019-09582-9 |
| Popis: | 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. |
| Databáze: | OpenAIRE |
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