UNIT 4.21 Uridine 2′-Carbamates: Facile Tools for Oligonucleotide 2′-Functionalization
Published Online: 1 FEB 2004
Copyright © 2003 by John Wiley and Sons, Inc.
Lab Protocol Title
Current Protocols in Nucleic Acid Chemistry
How to Cite
Korshun, V. A., Stetsenko, D. A. and Gait, M. J. 2004. Uridine 2′-Carbamates: Facile Tools for Oligonucleotide 2′-Functionalization. Current Protocols in Nucleic Acid Chemistry. 15:4.21:4.21.1–4.21.26.
- Published Online: 1 FEB 2004
- Published Print: DEC 2003
A facile method for preparation of uridine 2′-carbamate derivatives based on reaction of 3′,5′-disilyl-protected uridine with 1,1′-carbonyldiimidazole followed by treatment with an aliphatic amine is presented. A phosphoramidite monomer suitable for automated oligonucleotide synthesis is obtained in a few steps. The compounds are useful for the introduction of various labels and modifications into an oligonucleotide chain. Although 2′-carbamate modification is somewhat destabilizing for DNA-DNA and DNA-RNA duplexes, it is suitable for the direction of ligands into the minor groove of duplexes or at non-base-paired sites (e.g., loops and bulges) of oligonucleotides. Pyrene-modified oligonucleotide 2′-carbamates show a considerable increase in fluorescence intensity upon hybridization to a complementary RNA (but not DNA).
- uridine carbamate;
- oligonucleotide modification;
- duplex stability;