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 > Department of Chemistry, Biochemistry and Pharmaceutical Sciences (DCBP) |
UniBE Contributor: |
Gerber, Anna-Barbara, 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: |
05 Dec 2022 14:27 |
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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