Universal solid supports for the synthesis of oligonucleotides via a transesterification of H-phosphonate diester linkage.
[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.
Ferreira
Fernando
F
Laboratoire de Chimie Organique Biomoléculaire de Synthèse, UMR 5625 CNRS-UM II, ERT Oligonucleotides: Methodologie Valorisation, Université de Montpellier II, CC008, Place E. Bataillon, 34095 Montpellier Cedex 5, France.
Meyer
Albert
A
Vasseur
Jean-Jacques
JJ
Morvan
François
F
D004951:Esterification; D004952:Esters / Q000737:chemistry*; D009841:Oligonucleotides / Q000138:chemical synthesis*; D063065:Organophosphonates / Q000737:chemistry*; D019032:Spectrometry, Mass, Matrix-Assisted Laser Desorption-Ionization
D004952:Esters; D009841:Oligonucleotides; D063065:Organophosphonates