PMID: 11906272Mar 22, 2002Paper

Synthesis and cleavage experiments of oligonucleotide conjugates with a diimidazole-derived catalytic center

Bioconjugate Chemistry
Birgit VerbeurePiet Herdewijn

Abstract

Ribonuclease mimics based on diimidazole derived constructs in combination with or without additional amino groups have been synthesized and conjugated to oligonucleotides. The imidazole moiety was used either unprotected, protected with a monomethoxytrityl group or a tert-butyloxy carbonyl group. Acylation reactions were carried out using the 3-acyl-1,3-thiazolidine-2-thione activation strategy. The peptides were coupled to the oligonucleotides with a mixture of PyBOP, DIEA an HOBt in DMF on solid support. The conjugates were purified by RP-HPLC and identified using negative ion mode mass spectrometry. Unfortunately, no cleavage of a linear RNA target under physiological conditions could be observed.

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Citations

Apr 15, 2011·Nucleosides, Nucleotides & Nucleic Acids·Anthony D Saleh, Paul S Miller
Aug 20, 2008·Nucleosides, Nucleotides & Nucleic Acids·Elzbieta Sochacka, Damian Smuga
Jan 6, 2004·Nucleic Acids Research·Sandra FouaceBrice Felden
Aug 19, 2007·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Mieke A Catry, Annemieke Madder
Dec 4, 2004·Organic Letters·Sylvie PicardPhilippe Uriac
Apr 22, 2009·Journal of the American Chemical Society·Jason M ThomasDavid M Perrin
May 20, 2009·Bioorganic & Medicinal Chemistry Letters·Carly GambleReynald Gillet
Dec 17, 2005·Organic & Biomolecular Chemistry·Teija Niittymäki, Harri Lönnberg
Nov 11, 2014·Beilstein Journal of Organic Chemistry·Vicky GheerardijnAnnemieke Madder
Aug 22, 2002·Journal of the American Chemical Society·Leonard LermerDavid M Perrin
Sep 14, 2006·Chemical Reviews·Natarajan Venkatesan, Byeang Hyean Kim

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