Phosphorimidazolide
Open-knowledge reference entry
A phosphorimidazolide is a chemical compound in which a phosphoryl mono-ester is covalently bound to a nitrogen atom in an imidazole ring. They are a type of phosphoramidate. These phosphorus (V) compounds are encountered as reagents used for making new phosphoanhydride bonds with phosphate mono-esters, and as reactive intermediates in phosphoryl transfer reactions in some enzyme-catalyzed transformations. They are also being studied as critical chemical intermediates for the polymerization of nucleotides in pre-biotic settings. They are sometimes referred to as phosphorimidazolidates, imidazole-activated phosphoryl groups, and P-imidazolides.
Role in oligonucleotide formation
Phosphorimidazolides have been investigated for their mechanistic role in abiogenesis (the natural process by which life arose from non-living matter). Specifically, they have been proposed as the active electrophilic species which may have mediated the formation of inter-nucleotide phosphodiester bonds, thereby enabling template-directed oligonucleotide replication before the advent of enzymes. Phosphorimidazolides were originally proposed as mediators of this process by Leslie Orgel in 1968. Early studies showed that divalent metal cations such as Mg2+, Zn2+, and Pb2+ and a complementary template were required for the formation of short oligonucleotides, although nucleotides exhibited 5'-2' connectivity instead of 5'-3' connectivity of present-day life forms. It was also shown that Montmorillonite clay could provide a surface for phosphorimidazolide-mediated oligonucleotide formation with lengths of 20-50 bases.
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