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

被引:2
作者
Lavado, Nieves [1 ]
Garcia de la Concepcion, Juan [1 ]
Babiano, Reyes [1 ]
Cintas, Pedro [1 ]
Light, Mark E. [2 ]
机构
[1] UEX, Fac Ciencias, Dept Quim Organ & Inorgan, Ave Elvas S-N, E-06006 Badajoz, Spain
[2] Univ Southampton, Dept Chem, Fac Nat & Environm Sci, Southampton SO17 1BJ, Hants, England
来源
ORIGINS OF LIFE AND EVOLUTION OF BIOSPHERES | 2019年 / 49卷 / 03期
关键词
Prebiotic chemistry; Amino acids; Aminoxazole chemistry; Reaction mechanism; Dipeptide; MOLECULAR-ORBITAL METHODS; GLYCOLALDEHYDE PHOSPHATE; ORIGIN; PRECURSORS; PEPTIDES; RNA; CHEMISTRY; SET; HOMOCHIRALITY; RECOGNITION;
D O I
10.1007/s11084-019-09582-9
中图分类号
Q [生物科学];
学科分类号
07 ; 0710 ; 09 ;
摘要
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.
引用
收藏
页码:163 / 185
页数:23
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