Details
| Original language | English |
|---|---|
| Pages (from-to) | 15365-15371 |
| Number of pages | 7 |
| Journal | Chemistry - A European Journal |
| Volume | 24 |
| Issue number | 57 |
| Early online date | 7 Aug 2018 |
| Publication status | Published - 12 Oct 2018 |
| Externally published | Yes |
Abstract
A DNA G-quadruplex adopting a (3+1)-hybrid structure was substituted at its 5′-tetrad by riboguanosine (rG) analogs. Incorporation of anti-favoring rG at appropriate syn-positions of the 5′-outer tetrad induced conformational rearrangements to yield a quadruplex featuring a 5′-tetrad with reversed polarity. A high-resolution structure of a disubstituted quadruplex variant as well as direct NMR experimental evidence reveals a non-conventional C−H⋅⋅⋅O hydrogen bond in a medium groove between the 2′-OH of an rG residue adopting a C2′-endo sugar pucker and H8 of a 3′-neighboring anti-G residue. In contrast, a C3′-endo sugar conformation for another guanine ribonucleotide prevents formation of a corresponding hydrogen bond but relocates its 2′-OH substituent from the quadruplex narrow groove into a medium groove. Both the formation of favorable CHO hydrogen bridges and unfavorable interactions of the 2′-hydroxyl group in a narrow groove will promote RNA folding into a parallel topology featuring all-anti core residues and four grooves of medium size.
Keywords
- DNA–RNA hybrids, G-quadruplexes, NMR spectroscopy, glycosidic torsion angle, pseudo-hydrogen bonds
ASJC Scopus subject areas
- Chemical Engineering(all)
- Catalysis
- Chemistry(all)
- Organic Chemistry
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In: Chemistry - A European Journal, Vol. 24, No. 57, 12.10.2018, p. 15365-15371.
Research output: Contribution to journal › Article › Research › peer review
}
TY - JOUR
T1 - DNA–RNA Hybrid Quadruplexes Reveal Interactions that Favor RNA Parallel Topologies
AU - Haase, Linn
AU - Dickerhoff, Jonathan
AU - Weisz, Klaus
N1 - Publisher Copyright: © 2018 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
PY - 2018/10/12
Y1 - 2018/10/12
N2 - A DNA G-quadruplex adopting a (3+1)-hybrid structure was substituted at its 5′-tetrad by riboguanosine (rG) analogs. Incorporation of anti-favoring rG at appropriate syn-positions of the 5′-outer tetrad induced conformational rearrangements to yield a quadruplex featuring a 5′-tetrad with reversed polarity. A high-resolution structure of a disubstituted quadruplex variant as well as direct NMR experimental evidence reveals a non-conventional C−H⋅⋅⋅O hydrogen bond in a medium groove between the 2′-OH of an rG residue adopting a C2′-endo sugar pucker and H8 of a 3′-neighboring anti-G residue. In contrast, a C3′-endo sugar conformation for another guanine ribonucleotide prevents formation of a corresponding hydrogen bond but relocates its 2′-OH substituent from the quadruplex narrow groove into a medium groove. Both the formation of favorable CHO hydrogen bridges and unfavorable interactions of the 2′-hydroxyl group in a narrow groove will promote RNA folding into a parallel topology featuring all-anti core residues and four grooves of medium size.
AB - A DNA G-quadruplex adopting a (3+1)-hybrid structure was substituted at its 5′-tetrad by riboguanosine (rG) analogs. Incorporation of anti-favoring rG at appropriate syn-positions of the 5′-outer tetrad induced conformational rearrangements to yield a quadruplex featuring a 5′-tetrad with reversed polarity. A high-resolution structure of a disubstituted quadruplex variant as well as direct NMR experimental evidence reveals a non-conventional C−H⋅⋅⋅O hydrogen bond in a medium groove between the 2′-OH of an rG residue adopting a C2′-endo sugar pucker and H8 of a 3′-neighboring anti-G residue. In contrast, a C3′-endo sugar conformation for another guanine ribonucleotide prevents formation of a corresponding hydrogen bond but relocates its 2′-OH substituent from the quadruplex narrow groove into a medium groove. Both the formation of favorable CHO hydrogen bridges and unfavorable interactions of the 2′-hydroxyl group in a narrow groove will promote RNA folding into a parallel topology featuring all-anti core residues and four grooves of medium size.
KW - DNA–RNA hybrids
KW - G-quadruplexes
KW - NMR spectroscopy
KW - glycosidic torsion angle
KW - pseudo-hydrogen bonds
UR - http://www.scopus.com/inward/record.url?scp=85053380813&partnerID=8YFLogxK
U2 - 10.1002/chem.201803367
DO - 10.1002/chem.201803367
M3 - Article
VL - 24
SP - 15365
EP - 15371
JO - Chemistry - A European Journal
JF - Chemistry - A European Journal
SN - 0947-6539
IS - 57
ER -