Bioconjugate Chemistry 2010-08-18

Synthesis and evaluation of new spacers for use as dsDNA end-caps.

Pei-Sze Ng, Brian M Laing, Ganesan Balasundarum, Maneesh Pingle, Alan Friedman, Donald E Bergstrom

Index: Bioconjug. Chem. 21(8) , 1545-53, (2010)

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Abstract

A series of aliphatic and aromatic spacer molecules designed to cap the ends of DNA duplexes have been synthesized. The spacers were converted into dimethoxytrityl-protected phosphoramidites as synthons for oligonucleotides synthesis. The effect of the spacers on the stability of short DNA duplexes was assessed by melting temperature studies. End-caps containing amide groups were found to be less stabilizing than the hexaethylene glycol spacer. End-caps containing either a terthiophene or a naphthalene tetracarboxylic acid diimide were found to be significantly more stabilizing. The former showed a preference for stacking above an A*T base pair. Spacers containing only methylene (-CH(2)-) and amide (-CONH-) groups interact weakly with DNA and consequently may be optimal for applications that require minimal influence on DNA structure but require a way to hold the ends of double-stranded DNA together.