Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 80, Issue 14, Pages 7066-7075Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.5b00911
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Funding
- NSF
- NASA Astrobiology Program under the NSF Center for Chemical Evolution [CHE-1004570]
- NASA Astrobiology: Exobiology and Evolutionary Biology Program [NNX12AD62G]
- Simons Foundation [327124]
- NASA [52924, NNX12AD62G] Funding Source: Federal RePORTER
- Division Of Chemistry
- Direct For Mathematical & Physical Scien [1004570] Funding Source: National Science Foundation
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Uracil derivatives form strong complexes with complementary 2,4-diaminotriazine and adenine compounds, whereas derivatives of 5-azauracil (2,4-dioxotriazine) are known to form weak complexes in aqueous medium. However, herein we report that in organic medium (CDCl3), the 5-azauracil moiety forms hydrogen-bond-mediated complexes with complementary 2,4-diaminotriazine and adenine compounds, with strengths comparable to those formed by uracil compounds. Such dichotomous base-pairing behavior of the 5-azauracil moiety, in organic versus aqueous media, is found to be consistent with the ionization of the 5-azauracil moiety in aqueous medium leading to competitive interference from water molecules (via solvation), which is absent (lack of such ionization and solvent interference) in organic medium. This discriminating role of solvent (e.g., water) could have been an important factor in the selection of molecules, based on their physicochemical properties, and subsequently in the emergence of potential primordial informational oligomers that would have played a role in the origins of life.
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