ArticleThe Journal of organic chemistry2014
Solid-phase synthesis and hybrization behavior of partially 2'/3'-O-acetylated RNA oligonucleotides.
Article in The Journal of organic chemistry, 2014. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 5 papers.
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Who cites it
5 citing papers in PubMed.
- Site-Specific Synthesis ofJournal of the American Chemical Society · 2022Article
- The chemistry and applications of RNA 2'-OH acylation.Nature reviews. Chemistry · 2020Article
- Polyacetate and Polycarbonate RNA: Acylating Reagents and Properties.Organic letters · 2019Article
- pH-Driven RNA Strand Separation under Prebiotically Plausible Conditions.Biochemistry · 2018Article
- Preparation of trinucleotide phosphoramidites as synthons for the synthesis of gene libraries.Beilstein journal of organic chemistry · 2018Review
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Authors and funding
4 authors.
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Abstract
Synthesis of partially 2'/3'-O-acetylated oligoribonucleotides has been accomplished by using a 2'/3'-O-acetyl orthogonal protecting group strategy in which non-nucleophilic strong-base (DBU) labile nucleobase protecting groups and a UV-light cleavable linker were used. Strong-base stability of the photolabile linker allowed on-column nucleobase and phosphate deprotection, followed by a mild cleavage of the acetylated oligonucleotides from the solid support with UV light. Two 17nt oligonucleotides, which were synthesized possessing one specific internal 2'- or 3'-acetyl group, were used as synthetic standards in a recent report from this laboratory detailing the prebiotically plausible ligation of RNA oligonucleotides. In order to further investigate the effect of 2'/3'-O-acetyl groups on the stability of RNA duplex structure, two complementary bis-acetylated RNA oligonucleotides were also expediently obtained with the newly developed protocols. UV melting curves of 2'-O-acetylated RNA duplexes showed a consistent ~3.1 °C decrease in Tm per 2'-O-acetyl group.
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