Synthesis and incorporation of a furan-modified adenosine building block for DNA interstrand crosslinking

Anup M Jawalekar; Marieke Op de Beeck; Floris L van Delft; Annemieke Madder

doi:10.1039/c0cc04667a

Synthesis and incorporation of a furan-modified adenosine building block for DNA interstrand crosslinking

Chem Commun (Camb). 2011 Mar 14;47(10):2796-8. doi: 10.1039/c0cc04667a. Epub 2011 Feb 2.

Authors

Anup M Jawalekar¹, Marieke Op de Beeck, Floris L van Delft, Annemieke Madder

Affiliation

¹ Institute for Molecules and Materials, Radboud University Nijmegen, Heyendaalseweg 135, NL-6525 AJ, Nijmegen, The Netherlands.

PMID: 21286656
DOI: 10.1039/c0cc04667a

Abstract

2'-O-(3-(Furan-2-yl)propyl)adenosine was synthesized and evaluated for interstrand crosslink (ICL) formation in DNA duplexes. In situ oxidation of the furan moiety with NIS showed rapid crosslink formation to dA and dC, while dT and dG were inactive.

MeSH terms

Adenosine / analogs & derivatives*
Adenosine / chemical synthesis*
Adenosine / chemistry*
Base Sequence
Bromosuccinimide / chemistry
Cross-Linking Reagents / chemical synthesis*
Cross-Linking Reagents / chemistry*
DNA / chemistry*
DNA / genetics
Furans / chemical synthesis*
Furans / chemistry*
Oxidation-Reduction
Succinimides / chemistry

Substances

2'-O-(3-(furan-2-yl)propyl)adenosine
Cross-Linking Reagents
Furans
Succinimides
N-iodosuccinimide
DNA
Adenosine
Bromosuccinimide