Phosphorylation is a very important biochemical process utilized in metabolism and biochemical marking. The process of phosphorylation is thought to occur via enzymatic catalysis involving various phosphoesterases and kinases and the use of activated phosphates. We reported that the activation of phosphates toward phosphoesterification is a spontaneous non-enzymatic process which leads to the formation of the elusive pentacoordinated phosphoranes.Water soluble aldehydes and ketones combine with basic inorganic/organophosphates to form dioxaphosphetanes. Dioxaphosphetanes are activated phosphates that polymerize or phosphorylate alcohols without the requirement of any enzyme or additional activating agent. In five and six carbon monosaccharides, the activation-esterification occurs spontaneously and internally to give rise to the monosaccharide phosphorane. The pentacoordinated phosphoranes are then converted to the more stable phosphates via reductive dehydration.<br/>During the polymerization of inorganic phosphates, we observed that monobasic phosphates dimerize, dibasic phosphates form straight chain polymers while the tribasic phosphates formed three-prong polymers. Thus, the type of polymerization depends on the basicity of the phosphate. This led us to us believe that a correct combination of phosphates of the right basicities would produce biologically important polymers like ATP, ADP and DNA. Indeed, we successfully achieved good yields of the precursors of the diphosphates and triphosphates of inorganic phosphates and combinations of dialkyl phosphates and inorganic phosphates. Conditions for the synthesis of precursors of the diphosphates and triphosphates of monoalkyl phosphates (ATP, GTP) as well as posible stepwise synthesis of nucleic acids are being optimised and will be discussed.

Non-enzymatic synthesis of biologically important phosphates and polyphosphates

Macromolecular Chemistry: The Second Century

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ACS Spring 2020 National Meeting & Expo

The official archive and repository for all ACS Meetings & Expositions abstracts and select posters or presentations.