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Bioorg Med Chem Lett. 2003 Mar 10;13(5):847-50.

Oligonucleotides containing a new type of acyclic, achiral nucleoside analogue: 1-[3-hydroxy-2-(hydroxymethyl)prop-1-enyl]thymine.

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1
Department of Chemistry, The H. C. ├śrsted Institute, University of Copenhagen, Universitetsparken 5, DK-2100 Copenhagen, Denmark.

Abstract

An achiral, acyclic nucleoside analogue has been incorporated once or twice in oligodeoxyribonucleotides by the phosphoramidite method, and conditions found which allow deprotection of the oligonucleotides containing a sensitive modified allylic unit. The binding affinity of the modified oligonucleotides towards complementary DNA and RNA was reduced compared to unmodified DNA (DeltaT(m) -2 to -6.5 degrees C). An oligonucleotide with two modifications at the 3'-end showed considerable resistance towards cleavage with a 3'-exonuclease.

PMID:
12617905
[Indexed for MEDLINE]
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