Luminescence detection of tightly bound stacking aggregates of adenine and adenosine in aqueous solutions—the candidates for the role of the first genetic templates

Rapoport, V. L.; Malkin, V. M.; Zorina, S. V.; Komarov, S. M.; Goryuchko, V. V.

doi:10.1134/s1607672906010078

Cited by 2 publications

(2 citation statements)

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“…This is consistent with the current interpretation of the formation of purine stacks in water solution, which is based on various analytical techniques including nuclear magnetic resonance. 11,12,16 Taken together, all these data validate the turbidity measurement as a quantitative assay for the selfaggregation of adenine.…”

Section: Validation Of the Adenine Aggregation Assaysupporting

confidence: 56%

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Controlled aggregation of adenine by sugars: physicochemical studies, molecular modelling simulations of sugar–aromatic CH–π stacking interactions, and biological significance

Maresca

Derghal

Carravagna

et al. 2008

Phys. Chem. Chem. Phys.

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CH-Pi stacking interactions between carbohydrates and aromatic compounds play a central role in biomolecular recognition, especially in lectin-sugar and protein-glycolipid systems. In the present study, we have measured the solubility of the sparingly soluble aromatic base adenine in presence of various saccharides as an approach to investigate the interaction between adenine and sugars. Above 82.5 mM, adenine solutions gradually formed a crystalline precipitate which could be quantified by spectrophotometric turbidity measurements. Precipitation of adenine was increased by salts (NaCl and NaF) whereas it was prevented by DMSO, in agreement with the involvement of hydrophobic interactions (pi-pi stacking) in the vertical stacking of adenine molecules. Several monosaccharides and disaccharides were found to increase adenine solubility, with the following order: D-galactose = D-lactose > D-sucrose > D-glucose = D-maltose > D-ribose > D-fructose. Molecular mechanics simulations indicated that the potent cosolvent effect of beta-D-galactopyranose was probably mediated by CH-pi stacking interactions between its apolar surface and the aromatic structure of adenine. The polar OH groups of the sugars interacted with surrounding water molecules, ensuring the solubility of sugar-adenine complexes. In contrast, beta-D-fructofuranose, which has two polar faces, did not stack onto adenine and had a weak cosolvent effect. CH-pi stacking interactions were also demonstrated between 6-methylpurine and the sugar head group of glycolipids (glucosyl-, galactosyl- and lactosylceramide) but not with the charged head group of phosphatidylinositol-4,5-diphosphate. These data indicate that galactose-containing molecules have a high stacking propensity for aromatic compounds such as adenine, due to the specific structure of the galactose cycle.

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Section: Validation Of the Adenine Aggregation Assaysupporting

confidence: 56%

“…They were of the highest purity available, cell culture tested and used without further purification as validated in previous studies. 12 In all experiments, HPLC grade water (Carlo Erba, Val de Reuil, France) was used. ELISA microtiter plates were from Dominique Dutscher (Brumath, France).…”

Section: Methodsmentioning

confidence: 99%