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Paper Highlights

A Benzophenone‐Based Photocaging Strategy for the N7 Position of Guanosine

Lea Anhäuser, Nils Klöcker, Fabian Muttach, Florian Mäsing, Petr Špaček, Armido Studer and Andrea Rentmeister

Angewandte Chemie International Edition 2020, 59, 3161-3165.
https://doi.org/10.1002/anie.201914573 (open access)

Aryl ketones are photolabile caging groups if installed at the N7 position of guanosine or the N1 position of adenosine whereas common photocaging groups derived from the ortho‐nitrobenzyl moiety were not suitable.


Micellar Brønsted Acid Mediated Synthesis of DNA-Tagged Heterocycles

M. Klika Škopić, K. Götte, C. Gramse, M. Dieter, S. Pospich, S. Raunser, R. Weberskirch, A. Brunschweiger

https://doi.org/10.1021/jacs.9b05696

DNA-encoded libraries are increasingly used of drug identification. However, the reactivity of the DNA imposes limitations on the choice of chemical methods for encoded library synthesis. Amphiphilic block copolymers covalently functionalized with sulfonic acid moieties in the lipophilic portion assemble in water and locate the Brønsted catalyst in micelles. These acid nanoreactors enabled the reaction of DNA-conjugated aldehydes to diverse substituted tetrahydroquinolines and aminoimidazopyridines by Povarov and Groebke–Blackburn–Bienaymé reactions, respectively.

Rolling circle amplification shows a sinusoidal template length-dependent amplification bias

Bastian Joffroy, Yavuz O. Uca, Domen Prešern, Jonathan P. K. Doye, Thorsten L. Schmidt

Nucleic Acids Res. 2018, DOI:10.1093/nar/gkx1238

Small DNA circles can serve as templates for rolling circle amplification (RCA), which is a common and extremely robust amplification mechanism for nucleic acids. We discovered a strong template length-dependent amplification efficiency bias of RCA with the same periodicity as B-DNA.

 

 

A cytidine phosphoramidite with protected nitroxide spin label: Synthesis of a full-Length TAR RNA and investigation by in-line probing and EPR spectroscopy

Timo Weinrich, Eva A. Jaumann, Ute Scheffer, Thomas F. Prisner, Michael W. Göbel

Chem. Eur. J. 2018, DOI:10.1002/chem.201800167

A photolabile 2-nitrobenzyloxy methyl group can protect nitroxide spin labels against all critical conditions of chemical RNA synthesis and enzymatic strand ligation.

 


Structural transformation of wireframe DNA origami via DNA polymerase assisted gap-filling

Nayan P. Agarwal, Michael Matthies, Bastian Joffroy, Thorsten L. Schmidt
 
ACS Nano 2018, DOI:10.1021/acsnano.7b08345
 
In this work, we have explored the possibility to synthesize the complementary sequences to single-stranded gap regions in the DNA origami scaffold cost effectively by a DNA polymerase rather than by a DNA synthesizer.
 
 

Reversible modification of DNA by methyltransferase-catalyzed transfer and light-triggered removal of photo-caging groups

L. Anhäuser, F. Muttach, A. Rentmeister
 
Chem. Commun. 2018, DOI:10.1039/C7CC08300A

Methyltransferases are powerful tools for site-specific transfer of non-natural functional groups from synthetic analogs of their cosubstrate S-adenosyl-L-methionine (AdoMet). We present a new class of AdoMet analogs containing photo-caging (PC) groups in their side chain, enzymatic transfer of PC groups by a promiscuous DNA MTase as well as light-triggered removal from the target DNA. This strategy provides a new avenue to reversibly modulate the functionality of DNA at MTase target sites.
 


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