UV photostability of three 2-aminoazoles with key roles in prebiotic chemistry on the early earth?

Chemical Communications Pub Date: 2019-08-05 DOI: 10.1039/C9CC05265H

Abstract

Three related molecules in the 2-aminoazole family are potentially important for prebiotic chemistry: 2-aminooxazole, 2-aminoimidazole, and 2-aminothiazole, which can provide critical functions as an intermediate in nucleotide synthesis, a nucleotide activating agent, and a selective agent, respectively. Here, we examine the wavelength-dependent photodegradation of these three molecules under mid-range UV light (210–290 nm). We then assess the implications of the observed degradation rates for the proposed prebiotic roles of these compounds. We find that all three 2-aminoazoles degrade under UV light, with half lives ranging from ≈7–100 hours under a solar-like spectrum. 2-Aminooxazole is the least photostable, while 2-aminoimidazole is the most photostable. The relative photostabilities are consistent with the order in which these molecules would be used prebiotically: AO is used first to build nucleotides and AI is used last to activate them.

Graphical abstract: UV photostability of three 2-aminoazoles with key roles in prebiotic chemistry on the early earth
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