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Issue 14, 2014
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Design, synthesis and properties of artificial nucleic acids from (R)-4-amino-butane-1,3-diol

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Abstract

A new artificial nucleic acid analogue, (R)-Am-BuNA, was developed with a simplified acyclic (R)-4-amino-butane-1,3-diol phosphodiester backbone. Phosphoramidite monomers of (R)-Am-BuNA were incorporated into DNA oligonucleotides (ODNs) and G-quadruplexes. Their thermal stability, conformation change and biological stability were further investigated using UV-melting, circular dichroism (CD) and gel electrophoresis. The results suggested that thermal stability of the duplexes of (R)-Am-BuNA modified ODNs and their complementary ODN is highly dependent on the substitution position. Substitution of thymidine at the 7th position in a thrombin-binding DNA aptamer (TBA) results in a slight increase in Tm with no effect on quadruplex conformation on the CD spectrum in comparison to that of the natural G-quadruplex. Further enzymatic experiments with fetal bovine serum (FBS) and snake venom phosphodiesterase (SVPDE) indicated that only single replacement of a (R)-Am-BuNA modified nucleobase greatly inhibited oligonucleotide degradation, which shows their promising applications as capping nucleotides in nucleic acid drugs.

Graphical abstract: Design, synthesis and properties of artificial nucleic acids from (R)-4-amino-butane-1,3-diol

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Publication details

The article was received on 17 Nov 2013, accepted on 30 Jan 2014 and first published on 31 Jan 2014


Article type: Paper
DOI: 10.1039/C3OB42291G
Citation: Org. Biomol. Chem., 2014,12, 2263-2272
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    Design, synthesis and properties of artificial nucleic acids from (R)-4-amino-butane-1,3-diol

    P. Li, J. Sun, M. Su, X. Yang and X. Tang, Org. Biomol. Chem., 2014, 12, 2263
    DOI: 10.1039/C3OB42291G

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