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Silicate-Promoted Phosphorylation of Glycerol in Non-Aqueous Solvents: A Prebiotically Plausible Route to Organophosphates

1
University of South Florida, 4202 E Fowler Ave. NES 204, Tampa, FL 33584, USA
2
Department of Chemistry and Chemical Biology, Harvard University, 12 Oxford Street, Cambridge, MA 02138, USA
3
Georgia Institute of Technology, 315 Ferst Drive, Atlanta, GA 30332, USA
*
Author to whom correspondence should be addressed.
Received: 26 April 2017 / Revised: 20 June 2017 / Accepted: 23 June 2017 / Published: 29 June 2017
(This article belongs to the Special Issue Phosphorus (P) and the Origins of Life)
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Abstract

Phosphorylation reactions of glycerol were studied using different inorganic phosphates such as sodium phosphate, trimetaphosphate (a condensed phosphate), and struvite. The reactions were carried out in two non-aqueous solvents: formamide and a eutectic solvent consisting of choline-chloride and glycerol in a ratio of 1:2.5. The glycerol reacted in formamide and in the eutectic solvent with phosphate to yield its phosphorylated derivatives in the presence of silicates such as quartz sand and kaolinite clay. The reactions were carried out by heating glycerol with a phosphate source at 85 °C for one week and were analyzed by 31P-nuclear magnetic resonance (NMR) spectroscopy and mass spectrometry (MS). The yield of the phosphorylated glycerol was improved by the presence of silicates, and reached 90% in some experiments. Our findings further support the proposal that non-aqueous solvents are advantageous for the prebiotic synthesis of biomolecules, and suggest that silicates may have aided in the formation of organophosphates on the prebiotic earth. View Full-Text
Keywords: prebiotic synthesis; phosphorylation; origin of life; deep eutectic solvents; formamide; mineral catalysis prebiotic synthesis; phosphorylation; origin of life; deep eutectic solvents; formamide; mineral catalysis
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Gull, M.; Cafferty, B.J.; Hud, N.V.; Pasek, M.A. Silicate-Promoted Phosphorylation of Glycerol in Non-Aqueous Solvents: A Prebiotically Plausible Route to Organophosphates. Life 2017, 7, 29.

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