Elsevier

Carbohydrate Research

Volume 402, 30 January 2015, Pages 241-244
Carbohydrate Research

Note
Stabilization of ribofuranose by a mineral surface

https://doi.org/10.1016/j.carres.2014.07.018Get rights and content

Highlights

  • High thermal stabilization of d-ribose on silica surface.

  • The α-furanose form of d-ribose preferentially adsorbed on silica surface.

  • Solid state NMR studies of hybrid composites.

Abstract

The existence of the ribose moiety in biomolecules poses two problems for prebiotic chemistry. First, the exclusive presence of the furanose isomer in RNA has to be accounted for since furanose is a minor form in solution and does not exist in crystals. Second, all d-ribose polymorphs are unstable in aqueous medium so that a stabilization mechanism has to be invoked. We observed that the adsorption on mineral surfaces as amorphous silica protects the sugar from degradation processes. Moreover, this silica surface, used as realistic chert model, is able to increase significantly the proportion of ribofuranose compared to ribopyranose forms. The interaction between surface and sugar was analyzed by 13C NMR. Our results show a very significant chemical and thermal stabilization of the adsorbed sugar by a silica surface and an almost twofold increase of ribofuranose compared to ribose in solution.

Section snippets

Experimental

Ribose was provided by Sigma. Aerosil 380 (SiO2) was provided by Evonik. It is a non-porous fumed silica with a BET surface area of 380 m2/g.

Results and discussion

TGA (thermogravimetric analysis) of bulk d-ribose shows an endothermic event without weight change at 90 °C, due to ribose melting,13 followed by four weight-loss events (195 °C, about 20%, endothermic; 280 °C, weakly exothermic, and 320 °C, strongly exothermic, 51%; and 510 °C, around 29%, strongly exothermic and resulting in complete combustion; Fig. 1 and SI-Fig. 1). Here we do not intend to discuss these events in detail but to use them as a fingerprint. The endothermic weight loss at the low

Conclusion

The major result of our work is the stabilization of the d-ribose on the surface of silica, under drying and even under basic conditions. The adsorption and the drying process also significantly increase the proportion of furanose forms compared to ribose in solution. A more complete study on the physical chemistry of adsorbed ribose is underway taking into account the influence of cation complexation, and the relation of furanose and more specifically the β-d-ribofuranose selection with the

References (14)

  • W. Gilbert

    Nature

    (1986)
  • D. Ritson et al.

    Nat. Chem.

    (2012)
  • S.A. Benner et al.

    Acc. Chem. Res.

    (2012)
  • R. Shapiro

    Orig. Life Evol. Biosph.

    (1988)
  • R. Larralde et al.

    PNAS

    (1995)
  • D. Sisak et al.

    Angew. Chem., Int. Ed.

    (2010)
  • A. Ricardo et al.

    Science

    (2004)
    H.-J. Kim et al.

    J. Am. Chem. Soc.

    (2011)
There are more references available in the full text version of this article.

Cited by (0)

View full text