Synthesis and triplex forming properties of pyrrolidino pseudoisocytidine containing oligodeoxynucleotides

Mayer, Alain; Häberli, Adrian; Leumann, Christian J. (2005). Synthesis and triplex forming properties of pyrrolidino pseudoisocytidine containing oligodeoxynucleotides. Organic & biomolecular chemistry, 3(9), pp. 1653-1658. Royal Society of Chemistry 10.1039/B502799C

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Pyrrolidino pseudo-C-nucleosides are isosteres of natural deoxynucleosides which are protonated at the pyrrolidino ring nitrogen under physiological conditions. As constituents of a triplex forming oligodeoxynucleotide (TFO), the positive charge is expected to stabilise DNA triple helices via electrostatic interactions with the phosphodiester backbone of the target DNA. We describe the synthesis of the pyrrolidino isocytidine pseudonucleoside and the corresponding phosphoramidite building block and its incorporation into TFOs. Such TFOs show substantially increased DNA affinity compared to unmodified oligodeoxynucleotides. The increase in affinity is shown to be due to the positive charge at the pyrrolidino subunit

Item Type:

Journal Article (Original Article)

Division/Institute:

08 Faculty of Science > Departement of Chemistry and Biochemistry

UniBE Contributor:

Mayer, Alain and Leumann, Christian

Subjects:

500 Science > 570 Life sciences; biology
500 Science > 540 Chemistry

ISSN:

1477-0520

Publisher:

Royal Society of Chemistry

Language:

English

Submitter:

Christian Leumann

Date Deposited:

26 May 2014 14:56

Last Modified:

10 Aug 2015 10:47

Publisher DOI:

10.1039/B502799C

PubMed ID:

15858646

Uncontrolled Keywords:

backbone, Biochemistry, chemistry, deoxynucleoside, DNA Oligodeoxynucleotides, phosphoramidite, properties, synthesis, triple, Triplex

BORIS DOI:

10.7892/boris.53108

URI:

https://boris.unibe.ch/id/eprint/53108

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