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Iterative Synthesis of Nucleoside Oligophosphates with Phosphoramidites
Author(s) -
Cremosnik Gregor S.,
Hofer Alexandre,
Jessen Henning J.
Publication year - 2014
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201306265
Subject(s) - nucleoside , reagent , chemistry , combinatorial chemistry , nucleotide , coupling (piping) , organic chemistry , stereochemistry , materials science , biochemistry , metallurgy , gene
P‐Amidites can be used in iterative couplings to selectively give mixed P III –P V anhydrides. These intermediates can be oxidized followed by a rapid removal of the two terminal fluorenylmethyl groups. An iterative synthesis (coupling, oxidation, deprotection) of nucleoside oligophosphates can be carried out in solution and on a solid support. The coupling rates and yields are high, the procedures convenient (non‐dry reagents and solvents, ambient conditions, unprotected nucleotides), and the purification is very simple. The method works with all canonical nucleosides and holds promise for significant simplification of the usually cumbersome process of P‐anhydride bond construction.