@article{Choudhary2010,
abstract = {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 C2=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. {\textcopyright} 2010 American Chemical Society.},
author = {Choudhary, Amit and Kamer, Kimberli J. and Powner, Matthew W. and Sutherland, John D. and Raines, Ronald T.},
doi = {10.1021/cb100093g},
issn = {15548929},
journal = {ACS Chemical Biology},
number = {7},
pages = {655--657},
pmid = {20499895},
title = {{A stereoelectronic effect in prebiotic nucleotide synthesis}},
volume = {5},
year = {2010}
}

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