Preparation of pyridine-stretched 2′-deoxyhypoxanthosine phosphoramidite
Pyridine-stretched 2-deoxyhypoxanthosine (strH) phosphoramidite was prepared in eight steps from Hoffer's sugar (2-deoxy-3,5-di-O-(p-toluoyl)-a-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-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.
Clayton, Russell,Davis, Michael L.,Li, Wei,Fraser, William,Ramsden, Christopher A.
p. 87 - 104
(2017/06/19)
Template-directed DNA photoligation via α-5-cyanovinyldeoxyuridine
(Chemical Equation Presented) We describe an efficient template-directed photoligation of oligodeoxynucleotides (ODNs) using α-5- cyanovinyldeoxyuridine (αcU). An efficient photoligation was produced by photoirradiation of an ODN containing thymine at the 5′ end with an ODN containing thymine at the 5′ end in the presence of a template ODN. This photoligation method is a new and efficient way to synthesize branched ODNs.
Improved Syntheses of Halofuranose Derivatives with the Desired α-Configuration
Chlorination of ribofuranose or 2-deoxyribofuranose derivatives was carried out in a 1,4-dioxane solution of hydrogen chloride. This improved procedure allowed the syntheses of 1-chloro-α-D-ribofuranose and 1-chloro-2-deoxy-α-D-ribofuranose derivatives and offered ease of handling, high yield, and the stereo-controlled α-configuration at C-1.
Chin, Tsung-Mei,Huang, Liang-Kuen,Kan, Lou-Sing
p. 413 - 416
(2007/10/03)
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