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On the Prebiotic Synthesis of Ribonucleotides: Photoanomerisation of Cytosine Nucleosides and Nucleotides Revisited
Author(s) -
Powner Matthew W.,
Anastasi Carole,
Crowe Michael A.,
Parkes Alastair L.,
Raftery Jim,
Sutherland John D.
Publication year - 2007
Publication title -
chembiochem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.05
H-Index - 126
eISSN - 1439-7633
pISSN - 1439-4227
DOI - 10.1002/cbic.200700098
Subject(s) - cytidine , yield (engineering) , prebiotic , nucleotide , cytosine , chemistry , nucleoside , ribose , derivative (finance) , rna , stereochemistry , combinatorial chemistry , biochemistry , dna , enzyme , physics , gene , financial economics , economics , thermodynamics
Recent work has emphasised the importance of D ‐ribose aminooxazoline 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.