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Zn2+ Complexes of 3,5-Bis[(1,5,9-triazacyclododecan-3-yloxy)methyl]phenyl Conjugates of Oligonucleotides as Artificial RNases: The Effect of Oligonucleotide Conjugation on Uridine Selectivity of the Cleaving Agent




TekijätNiittymaki T, Burakova E, Laitinen E, Leisvuori A, Virta P, Lonnberg H

KustantajaWILEY-V C H VERLAG GMBH

Julkaisuvuosi2013

JournalHelvetica Chimica Acta

Lehden akronyymiHELV CHIM ACTA

Numero sarjassa1

Vuosikerta96

Numero1

Aloitussivu31

Lopetussivu43

Sivujen määrä13

ISSN0018-019X

DOIhttps://doi.org/10.1002/hlca.201200153


Tiivistelmä
2-(3,5-Bis{[1,5,9-tris(trifluoroacetyl)-1,5,9-triazacyclododecan-3-yloxy]methyl}phenoxy)ethanol was synthesized and converted to a O-(2-cyanoethyl)-N,N-diisopropylphosphoramidite building block, 12. 2'-O-Methyl oligoribonucleotides incorporating a 2-[(2S,4S,5R)-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)ethyl 4-oxopentanoate or a 2-{2-[2-({[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]acetyl}amino)ethoxy]ethoxy}ethyl 4-oxopentanoate non-nucleosidic unit close to the 3'-terminus were assembled on a solid support, the 4-oxopentanoyl protecting groups were removed by treatment with hydrazinium acetate on-support, and 12 was coupled to the exposed OH function. The deprotected conjugates were purified by HPLC, and their ability to cleave a complementary RNA containing either uridine or some other nucleoside at the potential cleaving site was compared. Somewhat unexpectedly, conjugation to an oligonucleotide did not enhance the catalytic activity of the Zn2+?bis(azacrown) complex and virtually abolished its selectivity towards the uridine sites.


Research Areas



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