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Plausible Prebiotic Synthesis of Aldopentoses from Simple Substrates, Glycolaldehyde and Formaldehyde

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Plausible Prebiotic Synthesis of Aldopentoses from Simple Substrates, Glycolaldehyde and Formaldehyde See discussions, stats, and author profiles for this publication at: https://www.researchgate.net/publication/259637530 Plausible prebiotic synthesis of aldopentoses from simple substrates, glycolaldehyde and formaldehyde Article in Paleontological Journal · December 2013 DOI: 10.1134/S0031030113090062 CITATION READS 1 57 3 authors: Irina Delidovich Oxana Taran RWTH Aachen University Boreskov Institute of Catalysis 53 PUBLICATIONS 1,539 CITATIONS 136 PUBLICATIONS 1,152 CITATIONS SEE PROFILE SEE PROFILE Valentin N Parmon Boreskov Institute of Catalysis 755 PUBLICATIONS 10,960 CITATIONS SEE PROFILE Some of the authors of this publication are also working on these related projects: Indo-Russia Joint project -Development of integrated (biotechnological and nanocatalytic) biorefinery for fuels and platform chemicals production from lignocellulosic biomass (crop/wood residues) View project In situ NMR of catalytic reactions View project All content following this page was uploaded by Oxana Taran on 20 July 2015. The user has requested enhancement of the downloaded file. ISSN 00310301, Paleontological Journal, 2013, Vol. 47, No. 9, pp. 1093–1096. © Pleiades Publishing, Ltd., 2013. Plausible Prebiotic Synthesis of Aldopentoses from Simple Substrates, Glycolaldehyde and Formaldehyde I. V. Delidovicha, O. P. Taranb, and V. N. Parmonc aBoreskov Institute of Catalysis, Siberian Branch, Russian Academy of Sciences, pr. akademika Lavrent’eva 5, Novosibirsk, 630090 Russia bNovosibirsk State Technical University, pr. K. Marksa, 20, Novosibirsk, 630073 Russia cNovosibirsk State University, ul. Pirogova 2, Novosibirsk, 630090 Russia email: [email protected] Received February 15, 2012 Abstract—Possible ways of abiotic catalytic synthesis of biologically significant aldopentoses (ribose, xylose, arabinose, lyxose) from elementary substrates, i.e., formaldehyde (FA) and glycolaldehyde (GA) in aqueous solutions are discussed. Conditions in which the process of synthesis of pentoses yields up to 65% relative to the initial concentration of GA: homogeneous borate catalyst NaOH + H3BO3, pH 9, [GA]0 5 mM, [FA]0 50–100 mM have been found. Keywords: prebiotic synthesis, aldopentoses, formaldehyde, borates, minerals DOI: 10.1134/S0031030113090062 INTRODUCTION et al., 2004) as a result of polymerization, dehydra The question of reaction conditions, in which bio tion, and destruction of carbohydrates. The low selec logically significant organic compounds (amino acids, tivity of this process casts doubt on the possibility that sugars, nucleotides, etc.) could have selectively been it could have yielded biologically significant carbohy synthesized from elementary substrates at prebiotic drates in sufficient concentration for further chemical developmental stages of the biosphere, is widely dis reactions, such as synthesis of ATP, nucleic acids, cussed. Terrestrial ponds, thermal springs, space dust, polysaccharides, etc. comets, and even protoplanet circumstellar disk were As was previously shown, the selectivity of synthe proposed among possible objects that could have been sis of monosaccharides increases as the reaction “reactors” for prebiotic synthesis. Therefore, the study occurs in alkalescent medium and in the absence of of chemical transformations of elementary com Ca2+ ions (Simonov, 2007). As a result of condensation pounds, yielding biologically significant substances, of FA with lower monosaccharides, i.e., glycolic (GA) enables the revelation of conditions, in which this syn and glyceric (GCA) aldehydes, and dihydroxyacetone thesis provides a rather large yield and, hence, supple (DHA), the formation of erythrulose and 3pentulose mentary arguments for certain models of prebiotic with the total yield ca. 75% was observed (Delidovich chemical evolution. et al., 2009; Simonov et al., 2007a, 2007b). It has been generally accepted for a long time that Monosaccharides of the aldopentose class (ribose, the most probable way of the synthesis of carbohy xylose, arabinose, lyxose) are stereoisomers differing drates from the simplest C1 substrate is the formose in spatial arrangement of hydroxyl and hydrogen reaction of condensation of formaldehyde (FA) in the groups. In modern biochemistry, aldopentoses play an important role, being the building blocks of polysac presence of Ca(OH)2 to give sugars. The presence of FA in prebiotic conditions seems rather probable; the charides, glycosides, natural gums, and slime; ribose, lowtemperature interaction of amorphous carbon which is included in ATP and RNA, is of particular with water results in the formation of hydroxymethyl importance. ene, isomerization of which produces FA (Ahmed In the present study, the possibility of synthesis of et al., 1983). However, a distinctive feature of the clas aldopentoses in a high yield in abiogenic conditions by sical formose reaction is simultaneous synthesis of sev catalytic condensation of GA with FA is analyzed. The eral dozen products, including linear and branched reaction of GA and FA was investigated in the pres sugars, organic acids, and polyols (Medvedeva et al., ence of homogeneous (phosphates, borates) and het 1983; Partridge et al., 1972). In addition, the reaction erogeneous (montmorillonites, apatite) catalysts, a mixture rapidly becomes yellowish brown (Riccardo sufficient amount of which could have been present on 1093 1094 DELIDOVICH et al. Probable structures of byproducts, branched CHO monosaccharides HO C CHOH CHOH CH2OH CH OH 2 CHO +FA CHOH CHO CHO +GA CHOH HO C CH2OH HO C CHOH CH2OH CHOH CH2OH CH2OH Pathway (1) CH2OH +FA CH2OH Aldopentoses CH OH +GCA CH2OH 2 +FA CHOH +GA CHO CH2OH CHOH CH OH GA CHO 2 C O C O C O +FA +FA GCA Pathway (2) CHOH CHOH Pathway (3) CH OH +Ga 2 CH2OH CH2OH DHA Erythrulose 3pentulose CHO CHOH CHOH CH2OH Aldotetroses Fig. 1. Pathways of synthesis of sugars from GA and FA in the presence of the basic catalysts. the prebiotic Earth. Note that the simplest lower (Kurgan deposits, 64% of humidity), and montmoril monosaccharide GA was recorded even in the inter lonite NaM (Azerbaijan, 85% of humidity). stellar space (Hollis et al., 2004); in terrestrial prebi otic conditions, it could have been formed as a result The values of pH in the reaction mixture were mea of a number of processes (Miller and Urey, 1959), for sured by pHmeter/ionomer Anion4101 (Infaspak example, photochemical condensation of FA in water Analit, Russia). During the experiment, reaction mix solutions (Pestunova et al., 2005). ture was sampled periodically to determine the con centrations of FA and carbohydrates by the highper formance liquid chromatography technique, with pre EXPERIMENTAL PART liminary derivatization of 2,4dinitrophenylhydrazine Experiments were performed in a deaerated ther (Cherstiouk et al., 2000), using a Milichrom A02 mostatically controlled (KRIOVT01 thermostat, chromatograph (Econova, Russia) with a ProntoSIL Russia) glass reactor, where 70 mL of solution of phos 1205C18 AQ column (75*2 mM) and a UV detector. phate or borate catalyst or water (if minerals were used as heterogeneous catalysts) were placed. Then, 21 mg of GA were solved (the initial concentration was RESULTS AND DISCUSSION 5 mM) and an appropriate aliquot of 7.33 M solution of FA (the initial concentration was 2.5–250 mM) was Figure 1 shows three main pathways of chemical charged into the reactor. In experiments with hetero reactions, in which GA and FA could be involved. geneous catalysts, 200 mg of mineral (calculated on Pathway (1) produces desirable products, aldopen dry weight) were added to the reaction mixture. Reac toses; pathway (2) gives erythrulose and 3pentulose; tions in the presence of homogeneous and heteroge and pathway (3) results in condensation of GA into neous catalysts lasted 8 and 52 h, respectively. Phos aldotetroses. In addition, reactions of interaction phates (0.2 M Na2HPO4 + KH2PO4, pH = 7.0; 8.0; between GA, GCA, and FA yielding branched 9.0) and borates (0.13 M H3BO3 + NaOH, pH = 9.0) monosaccharides are possible. This work was aimed at were tested as homogeneous catalysts and heteroge the search for the conditions, in which the rate of reac neous catalysts (minerals) were represented by apatite tions of pathway (1) prevails over the rates of all other (Kola Peninsula, Apatit), montmorillonite NaM processes. PALEONTOLOGICAL JOURNAL Vol. 47 No. 9 2013 PLAUSIBLE PREBIOTIC SYNTHESIS OF ALDOPENTOSES 1095 Products of Condensation of GA with FA (a) in the Presence of Different Catalysts Aldopentoses Aldotetroses Stoichiometric molar ratio of GA and FA in the 3Pentulose Erythrulose reactions of synthesis of aldopentoses (pathway 1) is Branched monosaccharides 2 : 1. However, preliminary results have shown that, 100 when the substrates interact in stoichiometric amounts, the rate of pathway (3) is considerably higher 80 than the rate of (1) (Fig. 2b), due to higher electrophi licity of GA in comparison with FA. In addition, it is 60 highly improbable that, in prebiotic conditions, the concentration of GA was higher than that of FA 40 because of high reactivity of GA. Therefore, the study Yield, % of the effect of the catalyst nature on the composition 20 of products was performed in conditions of the excess 0 of FA, with the molar ratio GA : FA = 1 : 5. The 1234567 dependence of the yield of reaction product on the Catalysts catalyst nature is shown in Fig. 2a. (b) In the presence of heterogeneous catalysts, the Aldopentoses Aldotetroses products accumulated at a slower rate than over homogeneous catalysts. The reaction rate over the Branched monosaccharides
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