On the prebiotic synthesis of ribonucleotides: Photoanomerisation of cytosine nucleosides and nucleotides revisited. Powner, M. W., Anastasi, C., Crowe, M. A., Parkes, A. L., Raftery, J., & Sutherland, J. D. ChemBioChem, 8(10):1170–1179, 2007. doi abstract bibtex Recent work has emphasised the importance of D-ribose amino-oxazoline 1 in the synthesis of cytidine ribonucleosides under potentially prebiotic conditions. Upon treatment with cyanoacetylene, 1 is transformed into $α$-D-cytidine ($α$-2), and if an efficient means of anomerising this nucleoside or a derivative thereof were to be found, then the synthesis of one of the key $β$-D-nucleosides required to make RNA would be realised. Photoanomerisation of $α$-2 has previously been described, but the yield was extremely low. Therefore, the present study was initiated to determine whether this low yield was the result of a low conversion or competing reaction pathways. © 2007 Wiley-VCH Verlag GmbH & Co. KGaA.
@article{Powner2007,
abstract = {Recent work has emphasised the importance of D-ribose amino-oxazoline 1 in the synthesis of cytidine ribonucleosides under potentially prebiotic conditions. Upon treatment with cyanoacetylene, 1 is transformed into $\alpha$-D-cytidine ($\alpha$-2), and if an efficient means of anomerising this nucleoside or a derivative thereof were to be found, then the synthesis of one of the key $\beta$-D-nucleosides required to make RNA would be realised. Photoanomerisation of $\alpha$-2 has previously been described, but the yield was extremely low. Therefore, the present study was initiated to determine whether this low yield was the result of a low conversion or competing reaction pathways. {\textcopyright} 2007 Wiley-VCH Verlag GmbH {\&} Co. KGaA.},
author = {Powner, Matthew W. and Anastasi, Carole and Crowe, Michael A. and Parkes, Alastair L. and Raftery, Jim and Sutherland, John D.},
doi = {10.1002/cbic.200700098},
issn = {14394227},
journal = {ChemBioChem},
keywords = {Nucleosides,Photoanomerisation,Photochemistry,Prebiotic,RNA},
number = {10},
pages = {1170--1179},
pmid = {17549787},
title = {{On the prebiotic synthesis of ribonucleotides: Photoanomerisation of cytosine nucleosides and nucleotides revisited}},
volume = {8},
year = {2007}
}
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