Issue 47, 2020

Post-synthetic transamination at position N4 of cytosine in oligonucleotides assembled with routinely used phosphoramidites

Abstract

The commercially available and cheap nucleotide phosphoramidites are routinely used for the oligonucleotide (ODN) assembly. T, isobutyryl-dG (iBudG), benzoyl-dA (BzdA), acetyl-dC (AcdC) and benzoyl-dC (BzdC) derivatives are sufficient to produce orthogonally protected ODNs. Clean and efficient (ca. 30%–70% yield) post-synthetic amination of an ODN assembled with such phosphoramidites was selectively achieved at the N4 position of a singly introduced BzdC. Such a method represents a novel and cheap strategy for the user-friendly post-modification of oligonucleotides at the internal position.

Graphical abstract: Post-synthetic transamination at position N4 of cytosine in oligonucleotides assembled with routinely used phosphoramidites

Supplementary files

Article information

Article type
Paper
Submitted
08 Here 2020
Accepted
03 Du 2020
First published
06 Du 2020

Org. Biomol. Chem., 2020,18, 9632-9638

Post-synthetic transamination at position N4 of cytosine in oligonucleotides assembled with routinely used phosphoramidites

R. Lartia, C. Vallée and E. Defrancq, Org. Biomol. Chem., 2020, 18, 9632 DOI: 10.1039/D0OB02059A

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