Preparation of pyridine-stretched 2’-deoxyhypoxanthosine phosphoramidite

Abstract

Pyridine-stretched 2(sic)-deoxyhypoxanthosine (strH) phosphoramidite was prepared in eight steps from Hoffer’s sugar (2(sic)-deoxy-3,5-di-O-(p-toluoyl)-alpha-D-erythro-pentofuranosyl chloride). Improved synthesis of the Hoffer sugar was achieved without need for distillation or chromatographic separation of intermediates, or use of gaseous HCl. Conditions were optimised to provide a key nitrile intermediate for the preparation of strH whereby the cesium salt of 4(5)-nitroimidazole was glycosylated using Hoffer’s sugar. The nitrile intermediate was also used to prepare pyridine-stretched 2(sic)-deoxyadenosine (strA) and pyridine-stretched 2(sic)-deoxy-2,6-diaminonebulamine (strD). Preliminary studies indicate that strH forms a stronger, size-expanded base pair with adenine compared with the Watson-Crick thymine-adenine base pair.

Citation

(2017). Preparation of pyridine-stretched 2’-deoxyhypoxanthosine phosphoramidite. Arkivoc, 87 -104. https://doi.org/10.3998/ark.5550190.p010.075

• Acceptance Date: Mar 24, 2017
• Publication Date: Apr 10, 2017
• Journal: ARKIVOC
• Print ISSN: 1551-7012
• Publisher: Michigan Publishing
• Pages: 87 -104
• DOI: https://doi.org/10.3998/ark.5550190.p010.075
• Keywords: 5-Aminoimidazoles, Hoffer’s sugar, pyridine-stretched purines, hypoxanthosine, phosphoramidite
• Publisher URL: http://dx.doi.org/10.3998/ark.5550190.p010.075