Issue 2, 2004
From the journal:

Organic & Biomolecular Chemistry

Synthesis and hybridization properties of l-oligodeoxynucleotide analogues fixed in a low antiglycosyl conformation†

Hidehito Urata,*a   Hidetaka Miyagoshi,a   Tetsuya Kumashiro,a   Takashi Yumoto,a   Keiji Mori,a   Keiko Shoji,a   Keigo Gohdab  and  Masao Akagi*a  

* Corresponding authors

a Osaka University of Pharmaceutical Sciences, 4-20-1 Nasahara, Takatsuki, Osaka 569-1094, Japan
E-mail: urata@gly.oups.ac.jp

b Computer-Aided Molecular Modeling Research Center Kansai, 2-8-20-404, Mikagehonmachi, Higashinada-ku, Kobe, Hyogo 658-0046, Japan

Abstract

We have synthesized L-type enantiomers (cU and cA) of nucleoside analogues, whose glycosyl bonds are fixed in a low anti conformation (ap glycosyl conformation, χ ≈ 180°), and incorporated them into oligonucleotides to evaluate the hybridization ability with natural DNA and RNA sequences. Although the incorporation of the modified nucleosides into oligonucleotides decreased the hybridization ability with unmodified complementary DNA sequences, the fully-substituted 12mers (cU12 and cA12) still retained the hybridization ability with the complementary unmodified DNA 12mers, regardless of their unnatural L-chirality. In contrast, cU12 and cA12 showed different hybridization behavior with complementary unmodified RNA 12mers. cU12 forms a more stable duplex with rA12 than the corresponding natural 12mer (dT12), whereas cA12 cannot hybridize with rU12. Based on the model structure of cU12–rA12, we discuss these experimental results.

Graphical abstract: Synthesis and hybridization properties of l-oligodeoxynucleotide analogues fixed in a low anti glycosyl conformation

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Article information

DOI
https://doi.org/10.1039/B312276J
Article type
Paper
Submitted
07 Oct 2003
Accepted
01 Dec 2003
First published
10 Dec 2003

Org. Biomol. Chem., 2004,2, 183-189

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Synthesis and hybridization properties of L-oligodeoxynucleotide analogues fixed in a low anti glycosyl conformation

H. Urata, H. Miyagoshi, T. Kumashiro, T. Yumoto, K. Mori, K. Shoji, K. Gohda and M. Akagi, Org. Biomol. Chem., 2004, 2, 183 DOI: 10.1039/B312276J

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