Synthesis of Nonnatural Oligonucleotides Made Exclusively of Alkynyl C-Nucleosides with Nonnatural Bases

Current Protocols in Nucleic Acid Chemistry
Junya Chiba, Masahiko Inouye

Abstract

This unit describes detailed procedures for the preparation of nonnatural C-nucleosides comprising seven types of nonnatural nucleobases attached to 1'-position of 2'-deoxyribose through an acetylene bond with the β-configuration. In addition, derivatization of these alkynyl C-nucleosides into the corresponding phosphoramidites and the subsequent oligonucleotide synthesis are also presented. The processes are depicted in three parts. The first basic protocol deals with the synthesis of a key intermediate, 5-O-DMTr-protected 1-ethynyl-2-deoxy-β-D-ribofuranoside. The second basic protocol mentions the procedures of the preparation of nonnatural C-nucleosides by a palladium-catalyzed coupling reaction of the ethynyl intermediate and halogen-attached nonnatural nucleobases. The synthetic procedures of the corresponding nonnatural phosporamidites are also described. The third basic protocol presents the solid-phase, automated synthesis of nonnatural oligonucleotides composed exclusively of the nonnatural C-nucleotides.

References

Oct 20, 2004·Accounts of Chemical Research·Steven A Benner
Feb 21, 2007·Accounts of Chemical Research·Andrew T KruegerEric T Kool
Oct 4, 2007·Organic Letters·Mauro F A Adamo, Roberto Pergoli
Jun 12, 2008·Journal of the American Chemical Society·Yasuhiro DoiMasahiko Inouye
Feb 13, 2010·Chemistry & Biodiversity·Junya Chiba, Masahiko Inouye
Feb 26, 2010·Nucleosides, Nucleotides & Nucleic Acids·Kevin W WellingtonSteven A Benner
Nov 20, 2013·Angewandte Chemie·Malte Winnacker, Eric T Kool

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Citations

Apr 4, 2019·Chembiochem : a European Journal of Chemical Biology·Yutaro OdaMasahiko Inouye

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