UNIT 2.12 Nucleobase Protection with Allyloxycarbonyl
Published Online: 1 JAN 2006
Copyright © 2005 by John Wiley and Sons, Inc.
Lab Protocol Title
Current Protocols in Nucleic Acid Chemistry
How to Cite
Hyodo, M. and Hayakawa, Y. 2006. Nucleobase Protection with Allyloxycarbonyl. Current Protocols in Nucleic Acid Chemistry. 23:2.12.1–2.12.26.
- Published Online: 1 JAN 2006
- Published Print: DEC 2005
This unit describes protocols for preparation of N-allyloxycarbonyl-protected 5′-O-(4,4′-dimethoxytrityl)-2′-deoxyribonucleosides and 2′-O-(tert-butyldimethylsilyl)-5′-O-(4,4′-dimethoxytrityl)ribonucleosides. These provide useful building blocks not only for synthesis of natural oligonucleotides but also for artificial analogs with chemically sensitive (particularly, base-labile) modified nucleoside bases or internucleotide linkages. These protected nucleosides are stable to conditions used for conversion to the corresponding nucleoside phosphoramidites and subsequent oligonucleotide synthesis, and the N-allyloxycarbonyl protecting group can be easily and cleanly removed by an organopalladium-catalyzed reaction under mild, nearly neutral conditions.
- protecting group;