Synthesis of Triazole‐Nucleoside Phosphoramidites and Their Use in Solid‐Phase Oligonucleotide Synthesis
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- Abstract
- Table of Contents
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- Literature Cited
Abstract
Triazole?backbone oligonucleotides are macromolecules that have one or more triazole units that are acting as a backbone mimic. Triazoles within the backbone have been used within oligonucleotides for a variety of applications. This unit describes the preparation and synthesis of two triazole?nucleoside phosphoramidites [uracil?triazole?uracil (UtU) and cytosine?triazole?uracil (CtU)] based on a PNA?like scaffold, and their incorporation within oligonucleotides. Curr. Protoc. Nucleic Acid Chem . 55:4.57.1?4.57.38. © 2013 by John Wiley & Sons, Inc.
Keywords: triazole?linkage; cycloaddition; phosphoramidite; solid?phase oligonucleotide synthesis
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PDF or HTML at Wiley Online LibraryTable of Contents
- Introduction
- Basic Protocol 1: Preparation of Uracil and Cytosine Pyrimidine Bases
- Basic Protocol 2: Preparation of Alkyne and Azide Linkers
- Basic Protocol 3: Preparation of Alkyne and Azide Monomers
- Basic Protocol 4: Preparation of Uracil‐Triazole‐Uracil Phosphoramidite (24)
- Basic Protocol 5: Preparation of Cytosine‐Triazole‐Uracil Phosphoramidite
- Basic Protocol 6: Synthesis, Purification, and Characterization of Oligonucleotides Containing CtU or UtU Units
- Reagents and Solutions
- Commentary
- Literature Cited
- Figures
- Tables
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Basic Protocol 1: Preparation of Uracil and Cytosine Pyrimidine Bases
Materials
Basic Protocol 2: Preparation of Alkyne and Azide Linkers
Materials
Basic Protocol 3: Preparation of Alkyne and Azide Monomers
Materials
Basic Protocol 4: Preparation of Uracil‐Triazole‐Uracil Phosphoramidite (24)
Materials
Basic Protocol 5: Preparation of Cytosine‐Triazole‐Uracil Phosphoramidite
Materials
Basic Protocol 6: Synthesis, Purification, and Characterization of Oligonucleotides Containing CtU or UtU Units
Materials
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Figure 4.57.1 General scheme for the conversion of uracil into uracil‐1‐yl acetic acid (2 ) and cytosine into ( N 4 ‐(benzoyl)cytosine‐1‐yl)acetic acid (5 ). View Image -
Figure 4.57.2 General scheme for the preparation of alkyne linker 8 and azide linkers 11 and 14 . View Image -
Figure 4.57.3 General scheme for the preparation of alkyne monomer 15 and azide monomers 16 and 19 . View Image -
Figure 4.57.4 General scheme for the preparation of the uracil‐triazole‐uracil dimer phosphoramidite (24 ). View Image -
Figure 4.57.5 General scheme for the preparation of the cytosine‐triazole‐uracil dimer phosphoramidite (27 ). View Image
Videos
Literature Cited
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