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

• Published in: Organic & biomolecular chemistry Vol. 18; no. 47; pp. 9632 - 9638
• Main Authors: Lartia, Rémy, Vallée, Coelio, Defrancq, Eric
• Format: Journal Article
• Language: English
• Published: CAMBRIDGE Royal Soc Chemistry 21.12.2020; Royal Society of Chemistry
• Subjects: Amination; Chemistry; Chemistry, Organic; Cytosine; Cytosine - chemistry; High-performance liquid chromatography; Liquid chromatography; Molecular Structure; Nucleotides; Oligonucleotides; Oligonucleotides - chemical synthesis; Oligonucleotides - chemistry; Organophosphorus Compounds - chemistry; Physical Sciences; Reaction products; Science & Technology; DNA; ACID; DEPROTECTION
• ISSN: 1477-0520; 1477-0539; 1477-0539
• DOI: 10.1039/d0ob02059a

The commercially available and cheap nucleotide phosphoramidites are routinely used for the oligonucleotide (ODN) assembly. T, isobutyryl-dG ( iBu dG), benzoyl-dA ( Bz dA), acetyl-dC ( Ac dC) and benzoyl-dC ( Bz dC) 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 Bz dC. Such a method represents a novel and cheap strategy for the user-friendly post-modification of oligonucleotides at the internal position. A novel strategy for the efficient and cheap post-modification of oligonucleotides at internal position.