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2 article(s) from Frei, Sibylle

Synthesis, biophysical properties, and RNase H activity of 6’-difluoro[4.3.0]bicyclo-DNA

Sibylle Frei,
Adam K. Katolik and
Christian J. Leumann

Beilstein J. Org. Chem. 2019, 15, 79–88, doi:10.3762/bjoc.15.9

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Figure 1: Chemical structure of selected fluorine-modified nucleic acids.

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Scheme 1: Synthesis of the bicyclic nucleoside 6. Reagents and conditions: a) BSA, thymine, NIS, DCM, 0 °C to...

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Scheme 2: Synthesis of the thymidine phosphoramidite building block 9. Reagents and conditions: a) HF-pyridin...

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Figure 2: X-ray structure of nucleoside 6a (left) and 6b (right).

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Figure 3: a) Potential energy profile versus pseudorotation phase angle of nucleoside 7 and b) its minimal en...

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Figure 4: CD spectra of ON1–4 with complementary a) DNA, and b) RNA. Total strand conc. 2 μM in 10 mM NaH₂PO₄...

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Figure 5: Hydrolysis products of the RNase H activation assay. The DNA served as positive control, whereas C1...

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Published 08 Jan 2019

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6’-Fluoro[4.3.0]bicyclo nucleic acid: synthesis, biophysical properties and molecular dynamics simulations

Sibylle Frei,
Andrei Istrate and
Christian J. Leumann

Beilstein J. Org. Chem. 2018, 14, 3088–3097, doi:10.3762/bjoc.14.288

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Figure 1: Chemical structure of selected nucleic acid analogs.

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Scheme 1: Synthesis of the gem-difluorinated glycal 4 from the silyl enol ethers 1α/β. Reagents and condition...

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Scheme 2: Synthesis of the thymidine phosphoramidite building block 10. Reagents and conditions: a) i) thymin...

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Scheme 3: Synthesis of the cytidine phosphoramidite building block 16. Reagents and conditions: a) Ac₂O, pyri...

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Figure 2: Proposed mechanism for the formation of the 5’-phosphorylated fragments during the oxidation step i...

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Figure 3: a) Potential energy profile versus pseudorotation phase angle of nucleoside 8 and its two minimal e...

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Figure 4: Average structures of the a) 6’F-bc^4,3-DNA/DNA, b) 6’F-bc^4,3-DNA/RNA, and c) 6’F-bc^4,3-DNA/6’F-bc^4,3...

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Figure 5: Preferred sugar pucker of a) 6’F-bc^4,3-DNA/DNA, and b) 6’F-bc^4,3-DNA/RNA duplexes and torsion angle...

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Published 20 Dec 2018

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