E-mail: exobio@mail.​Copanlisib nmr cytspb.​rssi.​ru Putative Prebiotic Photocatalytic Synthesis of Monosaccharides in Aqueous Solution of Formaldehyde Alexander Simonov1,2, Delidovich Irina1,2, Oxana Pestunova1,2,

Valery Snytnikov1,2, Valentin Parmon1,2 1Boreskov Institute of Catalysis; 2Novosibirsk State University An inestimable role in the organic life is played by carbohydrates. Monosaccharides and their derivates constitute the building blocks of various biomolecules like DNA and RNA, ATF, cellulose, chitin and starch which are indispensable for the living organisms. Among all prebiotic carbohydrates the main emphasis is placed on ribose. Indeed, the RNA-world (Gesteland and Atkins, 1993) is one of the most reasoned hypotheses on the prebiotic chemical evolution and the origin of life. In this work we investigated the possibility of formation of different monosaccharides from the simplest Vistusertib cost substrate—formaldehyde (hereinafter, FA), in the aqueous solution in possible prebiotic conditions. We demonstrated that glycolaldehyde (hereinafter, GA) could be formed in aqueous FA solution Ricolinostat under the UV-irradiation (Pestunova et al., 2005). From the other hand higher monosaccharides were shown to be synthesized

via condensation of formaldehyde and lower carbohydrates catalyzed by phosphates in neutral aqueous solution at mild temperatures. (Simonov et al., 2007). In order to combine these processes an experimental photo-catalytic flow installation was designed. Etomidate The starting

solution for all experiments contained FA with different concentrations and a catalyst-homogeneous phosphates (Na2HPO4 + KH2PO4), at pH = 8. That is, the sole substrate for the synthesis of monosaccharides was FA known to be an abundant compound of the prebiotic environment. The consecutive photosynthesis of GA and catalytic condensation of FA with lower monosaccharides resulted in the formation of significant amounts of higher monosaccharides. The HPLC analysis of the reaction mixture revealed that erythrulose (tetra-ketose) and 3-pentulose (penta-3-ketose) with maximum yields of 10% and 5%, respectively, were the major products of the process. At the same time the isomerization of 3-pentulose results in the formation of reasonable amounts of ribulose (4% yield). Finally, under the catalytic action of phosphates ribulose is isomerized into ribose and arabinose. The detected concentration of ribose in the reaction mixture was not very high. Nevertheless, it is the first evidence of the possibility of the synthesis of these vitally important monosaccharides from FA in putative prebiotic conditions. In addition to monosaccharides pyruvaldehyde was identified in the reaction mixture. Pyruvic acid was identified in trace amounts.