Unit

UNIT 1.18 Synthesis of Altritol Nucleoside Phosphoramidites for Oligonucleotide Synthesis

  1. Mikhail Abramov,
  2. Piet Herdewijn

Published Online: 1 SEP 2007

DOI: 10.1002/0471142700.nc0118s30

Current Protocols in Nucleic Acid Chemistry

Current Protocols in Nucleic Acid Chemistry

How to Cite

Abramov, M. and Herdewijn, P. 2007. Synthesis of Altritol Nucleoside Phosphoramidites for Oligonucleotide Synthesis. Current Protocols in Nucleic Acid Chemistry. 30:1.18:1.18.1–1.18.21.

Author Information

  1. Rega Institute for Medical Research, Leuven, Belgium

Publication History

  1. Published Online: 1 SEP 2007
  2. Published Print: SEP 2007

Abstract

This unit describes in detail the optimized preparations of altritol nucleoside phosphoramidite building blocks for oligonucleotide synthesis (aA, aG, aC, aU). d-Altritol nucleosides with adenine and uracil bases are obtained by nucleophilic opening of the epoxide ring of 1,5:2,3-dianhydro-4,6-O-benzylidene-d-allitol using the 1,8-diazabicyclo[5.4.0]undec-7-ene salts of the above-mentioned salts, while phase transfer catalysis (18-crown-6, K2CO3) is optimal for alkylation of 2-amino-6-chloropurine. The cytosine nucleoside is synthesized starting from the uracil congener. The 3′-hydroxyl function of hexitol sugar is protected with the benzoyl group. Curr. Protoc. Nucleic Acid Chem. 30:1.18.1-1.18.21. © 2007 by John Wiley & Sons, Inc.

Keywords:

  • altritol nucleic acid (ANA);
  • altritol nucleoside phosphoramidites;
  • aA;
  • aG;
  • aC;
  • aU