Journal
ACS CHEMICAL BIOLOGY
Volume 5, Issue 7, Pages 655-657Publisher
AMER CHEMICAL SOC
DOI: 10.1021/cb100093g
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Funding
- NIH [R01 AR044276]
- UK Engineering and Physical Sciences Research Council
- MRC [MC_UP_A024_1009] Funding Source: UKRI
- Medical Research Council [MC_UP_A024_1009] Funding Source: researchfish
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A plausible route for the spontaneous synthesis of an activated ribonucleotide that is poised for polymerization has been put forth (Powner et al. (2009) Nature, 459, 239-242). A key step in this route necessitates the regioselective phosphorylation of the secondary alcohol on C-3', of an anhydroarabinonucleoside in the presence of the primary alcohol on C-5'. Here, we propose that this regioselectivity relies on electron delocalization between a lone pair (n) of O-5' and an antibonding orbital (pi*) of C-2=N-3. This n ->pi* interaction modulates reactivity without the use of a protecting group. Thus, a stereoelectronic effect could have opened a gateway to the RNA world, the chemical milieu from which the first forms of life are thought to have emerged on Earth some 4 billion years ago.
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