On the Prebiotic Synthesis of Ribonucleotides: Photoanomerisation of Cytosine Nucleosides and Nucleotides Revisited | Zendy

Powner Matthew W. | Zendy; Anastasi Carole | Zendy; Crowe Michael A. | Zendy; Parkes Alastair L. | Zendy; Raftery Jim | Zendy; Sutherland John D. | Zendy

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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.

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