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Solid-phase Synthesis of [4.4] Spirocyclic Oximes
Published on: February 6, 2019
New solid support for the synthesis of 3'-oligonucleotide conjugates through glyoxylic oxime bond formation
Nicolas Spinelli1, Om Prakash Edupuganti, Eric Defrancq
1Département de Chimie Moléculaire, UMR CNRS 5250, ICMG FR2607, Université Joseph Fourier, BP 53, 38041 Grenoble Cedex 9, France.
Abstract:
A novel solid support 1 was synthesized to incorporate glyoxylic aldehyde functionality at the oligonucleotide 3'-terminus. 6-mer and 11-mer oligonucleotide sequences containing 3'-glyoxylic aldehyde functionality were prepared by using this support. These modified oligonucleotides were coupled to reporters containing an aminooxy group to prepare oligonucleotide 3'-conjugates through glyoxylic oxime bond formation. The hydrolytic stability of a glyoxylic oxime linkage was also investigated. [reaction: see text].
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