Jump to main content
Jump to site search

Issue 41, 2015
Previous Article Next Article

Synthesis of an oligonucleotide with a nicotinamide mononucleotide residue and its molecular recognition in DNA helices

Author affiliations

Abstract

Nicotinamide adenine dinucleotide (NAD) is a pivotal redox cofactor of primary metabolism. Its redox reactivity is based on the nicotinamide mononucleotide (NMN) moiety. We investigated whether NMN+ can engage in pairing interactions, when incorporated into an oligonucleotide. Here we describe the incorporation of NMN+ at the 3′-terminus of an oligodeoxynucleotide via a phosphoramidate coupling in solution. The stability of duplexes and triplexes with the NMN+-containing strand was measured in UV-melting curves. While the melting points of duplexes with different bases facing the nicotinamide were similar, triplex stabilities varied greatly between different base combinations, suggesting specific pairing. The most stable triplexes were found when a guanine and an adenine were facing the NMN+ residue. Their triplex melting points were higher than those of the corresponding triplexes with a thymidine residue at the same position. These results show that NMN+ residues can be recognized selectively in DNA helices and are thus compatible with the molecular recognition in nucleic acids.

Graphical abstract: Synthesis of an oligonucleotide with a nicotinamide mononucleotide residue and its molecular recognition in DNA helices

Back to tab navigation

Supplementary files

Publication details

The article was received on 14 Aug 2015, accepted on 04 Sep 2015 and first published on 04 Sep 2015


Article type: Paper
DOI: 10.1039/C5OB01714A
Author version
available:
Download author version (PDF)
Org. Biomol. Chem., 2015,13, 10303-10309
  • Open access: Creative Commons BY license
  •   Request permissions

    Synthesis of an oligonucleotide with a nicotinamide mononucleotide residue and its molecular recognition in DNA helices

    A. Göckel and C. Richert, Org. Biomol. Chem., 2015, 13, 10303
    DOI: 10.1039/C5OB01714A

    This article is licensed under a Creative Commons Attribution 3.0 Unported Licence. Material from this article can be used in other publications provided that the correct acknowledgement is given with the reproduced material.

    Reproduced material should be attributed as follows:

    • For reproduction of material from NJC:
      [Original citation] - Published by The Royal Society of Chemistry (RSC) on behalf of the Centre National de la Recherche Scientifique (CNRS) and the RSC.
    • For reproduction of material from PCCP:
      [Original citation] - Published by the PCCP Owner Societies.
    • For reproduction of material from PPS:
      [Original citation] - Published by The Royal Society of Chemistry (RSC) on behalf of the European Society for Photobiology, the European Photochemistry Association, and RSC.
    • For reproduction of material from all other RSC journals:
      [Original citation] - Published by The Royal Society of Chemistry.

    Information about reproducing material from RSC articles with different licences is available on our Permission Requests page.

Search articles by author

Spotlight

Advertisements