Abstract
Monosaccharides represent one of the major building blocks of life. One of the plausible prebiotic synthesis routes is the formose network, which generates sugars from C1 and C2 carbon sources in basic aqueous solution. We report on the feasibility of the formation of monosaccharides under physical forces simulated in a ball mill starting from formaldehyde, glycolaldehyde, DL-glyceraldehyde as prebiotically available substrates using catalytically active, basic minerals. We investigated the influence of the mechanic energy input on our model system using calcium hydroxide in an oscillatory ball mill. We show that the synthesis of monosaccharides is kinetically accelerated under mechanochemical conditions. The resulting sugar mixture contains monosaccharides with straight and branched carbon chains as well as decomposition products. In comparison to the sugar formation in water, the monosaccharides formed under mechanochemical conditions are more stable and selectively synthesized. Our results imply the possibility of a prebiotic monosaccharide origin in geochemical environments scant or devoid of water promoted by mechanochemical forces such as meteorite impacts or lithospheric activity.
Highlights
The formose reaction is the classical route to carbohydrates based on the oligomerization of formaldehyde (C1) through a cascade of cross, retro- and aldol reactions in aqueous solution in the presence of a basic catalyst, typically calcium hydroxide (Scheme 1) [1,2,3,4]
We report on the feasibility of the formation of monosaccharides under physical forces simulated in a ball mill starting from formaldehyde, glycolaldehyde, DL-glyceraldehyde as prebiotically available substrates using catalytically active, basic minerals
The formose reaction starts with formaldehyde and a base, most often calcium hydroxide, in aqueous solution
Summary
The formose reaction is the classical route to carbohydrates based on the oligomerization of formaldehyde (C1) through a cascade of cross-, retro- and aldol reactions in aqueous solution in the presence of a basic catalyst, typically calcium hydroxide (Scheme 1) [1,2,3,4]. The resulting product mixture contains sugars of different length, constitution, and configuration [5,6,7,8]. Isomerization and the instability of sugars under basic conditions are obstructive to the sugar formation in aqueous solutions [9,10]. The subsequent degradation reactions produce, for example, lactic acid, saccharic acid and α-dicarbonylic acids [11] and result in a dark tar-like substance.
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