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Org Lett. 2016 Jul 1;18(13):3222-5. doi: 10.1021/acs.orglett.6b01466. Epub 2016 Jun 16.

Chemoselective Dimerization of Phosphates.

Author information

1
Plant Biochemistry & Physiology Laboratory, Department of Botany and Plant Biology, University of Geneva , Quai E. Ansermet 30, 1211 Geneva, Switzerland.
2
Institute of Organic Chemistry, Albert-Ludwigs-University Freiburg , Albertstr. 21, 79104 Freiburg i. B., Germany.

Abstract

A methodology for the synthesis of oligophosphate conjugates using phosphordiamidites is described. This strategy facilitates the straightforward preparation of C2-symmetric dinucleoside tri-, penta-, and heptaphosphates. Moreover, unsymmetric compounds such as thiamine adenosine triphosphate and thiamine cytidine triphosphate can be prepared. The material is used to study the inhibitory activity of thiaminylated nucleotides against adenosine diphosphate ribosyltransferases.

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