Issue 5, 2012

Short-RNA selective binding of oligonucleotides modified using adenosine and guanosine derivatives that possess cyclohexylphosphates as substituents

Abstract

We have developed new artificial oligonucleotides which distinguish short RNA targets from long ones. The modification of the 5′ termini of oligonucleotides by using adenosine derivatives that possess a bulky cyclohexyl phosphate moiety at their base moiety and a phosphate group at the position of their 5′-hydroxyl group maximized their short RNA selectivity. The 2′-O-methyl-RNA (5′-XCmAmAmCmCmUmAmCmUm) having these modifications exhibits ca. 10 °C higher Tm in the duplexes with the complementary short RNA (3′-GUUGGAUGA-5′) than with the long RNA (3′-AUUAUAU[G with combining low line][U with combining low line][U with combining low line][G with combining low line][G with combining low line][A with combining low line][U with combining low line][G with combining low line][A with combining low line]UGGUUA-5′). The oligodeoxynucleotides having the same modification exhibited similar selectivity. Such short-RNA selective binding of terminally modified oligonucleotides can be employed to distinguish between mature microRNAs and pre-microRNAs.

Graphical abstract: Short-RNA selective binding of oligonucleotides modified using adenosine and guanosine derivatives that possess cyclohexyl phosphates as substituents

Supplementary files

Article information

Article type
Paper
Submitted
15 Sep 2011
Accepted
27 Oct 2011
First published
27 Oct 2011

Org. Biomol. Chem., 2012,10, 994-1006

Short-RNA selective binding of oligonucleotides modified using adenosine and guanosine derivatives that possess cyclohexyl phosphates as substituents

K. Seio, S. Kurohagi, E. Kodama, Y. Masaki, H. Tsunoda, A. Ohkubo and M. Sekine, Org. Biomol. Chem., 2012, 10, 994 DOI: 10.1039/C1OB06580G

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