News & Press

New Publication

Article addresses the synthesis of modified Nucleoside Oligophosphates

Sep 17, 2019

livMatS PI Prof. Dr. Henning Jessen and livMatS doctoral researcher Alexander Ripp have published a new paper on the synthesis of modified Nucleoside Oligophosphates in the Journal of the American Chemical Society.

The article´s abstract:

Phosphoramidite analogues of modified cyclotriphosphates provide a general and step-economical synthesis of nucleoside triphosphates and analogues on scale without the need for protecting groups. These reagents enable rapid access to pure nucleoside oligophosphates and a range of other analogues that were previously difficult to obtain (e.g., NH, CH2, CCl2, and CF2 replacements for O, phosphono- and phosphoimidazolides, -morpholidates, -azidates, and -fluoridates). DFT calculations demonstrate that the selectivity of the cyclotriphosphate opening reactions proceeds via an in-line substitution mechanism that displaces the least charged leaving group.

Synthesis of Modified Nucleoside Oligophosphates Simplified: Fast, Pure, and Protecting Group Free*
Jyoti Singh, Alexander Ripp, Thomas M. Haas, Danye Qiu, Manfred Keller, Paul A. Wender, Jay S. Siegel, Kim K. Baldridge and Henning J. Jessen
J. A. Chem. Soc. 2019, 141, doi: 10.1021/jacs.9b08273