Preparation of pyridine-stretched 2’-deoxyhypoxanthosine phosphoramidite

Abstract

Pyridine-stretched 2!-deoxyhypoxanthosine (strH) phosphoramidite was prepared in eight steps from Hoffer’s sugar (2!-deoxy-3,5-di-O-(p-toluoyl)-α-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!-deoxyadenosine (strA) and pyridine-stretched 2!-deoxy-diaminopurine (strD). Preliminary studies indicate that strH forms a stronger, size-expanded base pair with adenine compared with the Watson-Crick thymine-adenine base pair.

Publication DOI: https://doi.org/10.24820/ark.5550190.p010.075
Divisions: College of Health & Life Sciences > Aston Pharmacy School
College of Health & Life Sciences
College of Health & Life Sciences > School of Biosciences > Cell & Tissue Biomedical Research
Additional Information: © The authors. Creative Commons License Deed; Attribution-NonCommercial 4.0 International (CC BY-NC 4.0) https://creativecommons.org/licenses/by-nc/4.0/ Funding: Scotia Pharmaceuticals; Royal Society; and EPSRC Mass Spectrometry Cenre for high-resolution mass spectra. Copies of 1H and 13C NMR spectra are provided as supplementary material.
Uncontrolled Keywords: 5-aminoimidazoles,Hoffer’s sugar,pyridine-stretched purines,hypoxanthosine,phosphoramidite,Organic Chemistry
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Related URLs: http://www.scop ... tnerID=8YFLogxK (Scopus URL)
PURE Output Type: Article
Published Date: 2017-04-10
Accepted Date: 2017-03-24
Submitted Date: 2017-02-28
Authors: Clayton, Russell
Davis, Michael L.
Li, Wei
Fraser, William (ORCID Profile 0000-0001-6588-0166)
Ramsden, Christopher

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