On the prebiotic synthesis of ribonucleotides: photoanomerisation of cytosine nucleosides and nucleotides revisited.
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 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.
Powner
Matthew W
MW
School of Chemistry, The University of Manchester, Oxford Road, Manchester M13 9PL, UK.
Anastasi
Carole
C
Crowe
Michael A
MA
Parkes
Alastair L
AL
Raftery
Jim
J
Sutherland
John D
JD
D001671:Biochemistry / Q000379:methods; D002219:Carbamates / Q000737:chemistry; D003562:Cytidine / Q000737:chemistry; D003596:Cytosine / Q000737:chemistry*; D008027:Light; D009682:Magnetic Resonance Spectroscopy; D008954:Models, Biological; D008956:Models, Chemical; D009705:Nucleosides / Q000737:chemistry; D011714:Pyrans / Q000737:chemistry; D011741:Pyrimidine Nucleosides / Q000737:chemistry*; D011743:Pyrimidines / Q000737:chemistry; D012313:RNA / Q000737:chemistry; D012265:Ribonucleotides / Q000737:chemistry*; D013997:Time Factors
D002219:Carbamates; D009705:Nucleosides; D011714:Pyrans; D011741:Pyrimidine Nucleosides; D011743:Pyrimidines; D012265:Ribonucleotides; D003562:Cytidine; D012313:RNA; D003596:Cytosine