Stairs, S;
Powner, MW;
(2017)
Scalable Synthesis of 2,2′-Anhydro-arabinofuranosyl Imidazoles.
Synlett
, 28
(19)
pp. 2650-2654.
10.1055/s-0036-1590968.
Preview |
Text
Powner_paper_MWP_accepted_version.pdf - Accepted Version Download (386kB) | Preview |
Abstract
We report the efficient and scalable synthesis of 2,2′-anhydro-5-amino-1-β-arabinofuranosylimidazole-4-carboxamide and 2,2′-anhydro-5-amino-1-β-arabinofuranosylimidazole-4-carbonitrile from commercial arabino -adenosine. 2,2′-Anhydro-5-amino-1-β-arabinofuranosylimidazole-4-carboxamide is synthesised in only five steps with a single chromatographic purification. Additionally, we report a high-yielding, three-step conversion of 2,2′-anhydro-5-amino-1-β-arabinofuranosylimidazole-4-carboxamide into 2,2′-anhydro-5-amino-1-β-arabinofuranosylimidazole-4-carbonitrile. They are proposed key intermediates of the divergent prebiotic synthesis of ribonucleotides and this facile synthesis is anticipated to be instrumental in continued investigation of the origins of nucleotides.
Type: | Article |
---|---|
Title: | Scalable Synthesis of 2,2′-Anhydro-arabinofuranosyl Imidazoles |
Open access status: | An open access version is available from UCL Discovery |
DOI: | 10.1055/s-0036-1590968 |
Publisher version: | http://doi.org/10.1055/s-0036-1590968 |
Language: | English |
Additional information: | This version is the author accepted manuscript. For information on re-use, please refer to the publisher’s terms and conditions. |
Keywords: | AICAR, nucleosides, arabinosides, purines, prebiotic |
UCL classification: | UCL UCL > Provost and Vice Provost Offices > UCL BEAMS UCL > Provost and Vice Provost Offices > UCL BEAMS > Faculty of Maths and Physical Sciences UCL > Provost and Vice Provost Offices > UCL BEAMS > Faculty of Maths and Physical Sciences > Dept of Chemistry |
URI: | https://discovery.ucl.ac.uk/id/eprint/1560889 |
Archive Staff Only
View Item |