Unit

UNIT 2.12 Nucleobase Protection with Allyloxycarbonyl

  1. Mamoru Hyodo,
  2. Yoshihiro Hayakawa

Published Online: 1 JAN 2006

DOI: 10.1002/0471142700.nc0212s23

Current Protocols in Nucleic Acid Chemistry

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. 23:2.12:2.12.1–2.12.26.

Author Information

  1. Nagoya University, Nagoya, Japan

Publication History

  1. Published Online: 1 JAN 2006
  2. Published Print: DEC 2005

Abstract

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.

Keywords:

  • nucleoside;
  • oligonucleotide;
  • protecting group;
  • allyloxycarbonayl;
  • organopalladium