Oligoribonucleotides with 2'-O-(tert-butyldimethylsilyl) groups
1Ribozyme Pharmaceuticals, Boulder, Colorado, USA.
Current Protocols in Nucleic Acid Chemistry
|April 23, 2008
Summary
Chemical synthesis of RNA strands uses the phosphoramidite method, but the ribose sugar
Area of Science:
- Chemical Synthesis
- Oligonucleotide Chemistry
- Organic Chemistry
Background:
- Solid-phase chemical synthesis of oligoribonucleotides is commonly achieved using the phosphoramidite approach.
- The 2-hydroxyl group on the ribofuranosyl sugar moiety necessitates protection during this synthesis process.
Purpose of the Study:
- To describe methods for protecting the 2-hydroxyl group during oligoribonucleotide synthesis.
- To detail the use of the tert-butyldimethylsilyl (TBDMS) group for 2-OH protection.
Main Methods:
- Phosphoramidite chemical synthesis of oligoribonucleotides.
- Application of the TBDMS protecting group to the 2-hydroxyl position of ribofuranosyl sugars.
Main Results:
- Successful protection of the 2-OH group using the TBDMS protecting group.
- Facilitation of efficient oligoribonucleotide synthesis by managing the reactive 2-OH group.
Conclusions:
- The TBDMS group provides an effective method for protecting the 2-hydroxyl group in ribofuranosyl sugars.
- This protection strategy is crucial for the routine chemical synthesis of oligoribonucleotides via the phosphoramidite method.
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