Stairs, S;
Powner, MW;
(2017)
Scalable Synthesis of 2,2′-Anhydro-arabinofuranosyl Imidazoles.
Synlett
, 28
(19)
pp. 2650-2654.
10.1055/s-0036-1590968.
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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 |
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