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  • Title: Universal solid supports for the synthesis of oligonucleotides via a transesterification of H-phosphonate diester linkage.
    Author: Ferreira F, Meyer A, Vasseur JJ, Morvan F.
    Journal: J Org Chem; 2005 Nov 11; 70(23):9198-206. PubMed ID: 16268590.
    Abstract:
    [Structure: see text]. Three universal solid supports exhibiting an hydroxyl function were prepared. The introduction of a first H-phosphonate diester linkage which was kept throughout the elongation allowed the release of 3'-hydroxyl oligonucleotides by a transesterification mechanism. The transesterification was performed in a few minutes with either amino alcohols or K2CO3/methanol. Starting from a hydroxyl solid support, tandem oligonucleotides were synthesized and the solid support was easily recyclable. This strategy was extended to the release of an oligonucleotide from the solid support by a nonbasic treatment opening the way to the synthesis of base-sensitive oligonucleotides thanks to the selective deprotection of a hydroxyl in beta of the H-phosphonate diester linkage.
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