UNIT 1.18 Synthesis of Altritol Nucleoside Phosphoramidites for Oligonucleotide Synthesis
Published Online: 1 SEP 2007
Copyright © 2007 by John Wiley and Sons, Inc.
Lab Protocol Title
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.
- Published Online: 1 SEP 2007
- Published Print: SEP 2007
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.
- altritol nucleic acid (ANA);
- altritol nucleoside phosphoramidites;