Unit

UNIT 5.12 DNA Interstrand Cross-Link Formation Using Furan as a Masked Reactive Aldehyde

  1. Lieselot L.G. Carrette,
  2. Ellen Gyssels,
  3. Annemieke Madder

Published Online: 8 OCT 2013

DOI: 10.1002/0471142700.nc0512s54

Current Protocols in Nucleic Acid Chemistry

Current Protocols in Nucleic Acid Chemistry

How to Cite

Carrette, L. L., Gyssels, E. and Madder, A. 2013. DNA Interstrand Cross-Link Formation Using Furan as a Masked Reactive Aldehyde. Current Protocols in Nucleic Acid Chemistry. 54:5.12:5.12.1–5.12.16.

Author Information

  1. Organic and Biomimetic Chemistry Research Group, Department of Organic Chemistry, Ghent University, Krijgslaan, Ghent, Belgium

Publication History

  1. Published Online: 8 OCT 2013

Abstract

This unit describes a method for interstrand cross-linking between a furan-modified oligonucleotide and its unmodified complement. The synthesis of two furan-modified phosphoramidites, selected based on high cross-linking yield versus improved cross-linking selectivity, is described. The methods allow gram-scale synthesis starting from stable and readily available furan derivatives. Cross-linking requires selective oxidation of the furan moiety to an aldehyde. The masked nature of the latter avoids undesired and off-target reactions, resulting in clean and high-yield cross-link formation. Curr. Protoc. Nucleic Acid Chem. 54:5.12.1-5.12.16. © 2013 by John Wiley & Sons, Inc.

Keywords:

  • cross-linking;
  • oligonucleotide;
  • nucleoside;
  • furan