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Chemoselective multicomponent one-pot assembly of purine precursors in water.

Powner, MW; Sutherland, JD; Szostak, JW; (2010) Chemoselective multicomponent one-pot assembly of purine precursors in water. J Am Chem Soc , 132 (46) 16677 - 16688. 10.1021/ja108197s.

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Abstract

The recent development of a sequential, high-yielding route to activated pyrimidine nucleotides, under conditions thought to be prebiotic, is an encouraging step toward the greater goal of a plausible prebiotic pathway to RNA and the potential for an RNA world. However, this synthesis has led to a disparity in the methodology available for stepwise construction of the canonical pyrimidine and purine nucleotides. To address this problem, and further explore prebiotically accessible chemical systems, we have developed a high-yielding, aqueous, one-pot, multicomponent reaction that tethers masked-sugar moieties to prebiotically plausible purine precursors. A pH-dependent three-component reaction system has been discovered that utilizes key nucleotide synthons 2-aminooxazole and 5-aminoimidazoles, which allows the first divergent purine/pyrimidine synthesis to be proposed. Due to regiospecific aminoimidazole tethering, the pathway allows N9 purination only, thus suggesting the first prebiotically plausible mechanism for regiospecific N9 purination.

Type:Article
Title:Chemoselective multicomponent one-pot assembly of purine precursors in water.
Location:United States
DOI:10.1021/ja108197s
Language:English
Additional information:PMCID: PMC2984373
Keywords:Hydrogen-Ion Concentration, Molecular Structure, Purines, Pyrimidines, Water
UCL classification:UCL > School of BEAMS > Faculty of Maths and Physical Sciences > Chemistry

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