Unit

UNIT 4.40 Synthesis of Glycerol Nucleic Acid (GNA) Phosphoramidite Monomers and Oligonucleotide Polymers

  1. Su Zhang1,2,
  2. John C. Chaput1,2

Published Online: 1 SEP 2010

DOI: 10.1002/0471142700.nc0440s42

Current Protocols in Nucleic Acid Chemistry

Current Protocols in Nucleic Acid Chemistry

How to Cite

Zhang, S. and Chaput, J. C. 2010. Synthesis of Glycerol Nucleic Acid (GNA) Phosphoramidite Monomers and Oligonucleotide Polymers. Current Protocols in Nucleic Acid Chemistry. 42:4.40:4.40.1–4.40.18.

Author Information

  1. 1

    Department of Chemistry and Biochemistry, Arizona State University, Tempe, Arizona

  2. 2

    The Biodesign Institute at Arizona State University, Tempe, Arizona

Publication History

  1. Published Online: 1 SEP 2010
  2. Published Print: SEP 2010

Abstract

This unit describes a straightforward method for preparing glycerol nucleic acid (GNA) phosphoramidite monomers and oligonucleotide polymers using standard cyanoethyl phosphoramidite chemistry. GNA is an unnatural nucleic acid analog composed of an acyclic three-carbon sugar-phosphate backbone that contains one stereogenic center per repeating unit. GNA has attracted significant attention as a nucleic acid derivative due to its unique ability to form stable Watson-Crick anti-parallel duplex structures with thermal and thermodynamic stabilities rivaling those of natural DNA and RNA. The chemical simplicity of this nucleic acid structure provides access to enantiomerically pure forms of right- and left-handed helical structures that can be used as unnatural building blocks in DNA nanotechnology. Curr. Protoc. Nucleic Acid Chem. 42:4.40.1-4.40.18. © 2010 by John Wiley & Sons, Inc.

Keywords:

  • glycerol nucleic acid (GNA);
  • phosphoramidite;
  • oligonucleotide;
  • chemical synthesis;
  • solid-phase synthesis;
  • thermal stability;
  • nanotechnology