Synthesis and properties of isobicyclo-DNA

Gerber, Anna-Barbara; Leumann, Christian J. (2013). Synthesis and properties of isobicyclo-DNA. Chemistry - a European journal, 19(22), pp. 6990-7006. Wiley-VCH 10.1002/chem.201300487

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We present the synthesis of the isobicyclo-DNA building blocks with the nucleobases A, C, G and T, as well as biophysical and biological properties of oligonucleotides derived thereof. The synthesis of the sugar part was achieved in 5 steps starting from a known intermediate of the tricyclo-DNA synthesis. Dodecamers containing single isobicyclo-thymidine incorporations, fully modified A- and T-containing sequences, and fully modified oligonucleotides containing all four bases were synthesized and characterized. Isobicyclo-DNA forms stable duplexes with natural nucleic acids with a pronounced preference for DNA over RNA as complements. The most stable duplexes, however, arise by self-pairing. Isobicyclo-DNA forms preferentially B-DNA-like duplexes with DNA and A-like duplexes with complementary RNA as determined by circular dichroism (CD) spectroscopy. Self-paired duplexes show a yet unknown structure, as judged from CD spectroscopy. Biochemical tests revealed that isobicyclo-DNA is stable in fetal bovine serum and does not elicit RNaseH activity.

Item Type:

Journal Article (Original Article)

Division/Institute:

08 Faculty of Science > Departement of Chemistry and Biochemistry

UniBE Contributor:

Gerber, Anna-Barbara and Leumann, Christian

Subjects:

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

ISSN:

0947-6539

Publisher:

Wiley-VCH

Language:

English

Submitter:

Christian Leumann

Date Deposited:

08 Jan 2014 16:38

Last Modified:

13 Jul 2015 07:28

Publisher DOI:

10.1002/chem.201300487

PubMed ID:

23613358

Uncontrolled Keywords:

DNA, nucleosides, oligonucleotides, RNA, serum stability

BORIS DOI:

10.7892/boris.39684

URI:

https://boris.unibe.ch/id/eprint/39684

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