Changed reactivity of secondary hydroxy groups in C8-modified adenosine – lessons learned from silylation

• Jennifer Frommer and
• Sabine Müller

Beilstein J. Org. Chem. 2020, 16, 2854–2861, doi:10.3762/bjoc.16.234

• being preferentially formed. Optimization of the protection scheme lead to a new and economic route to the desired C8-alkynylated building block and its incorporation in RNA. Keywords: nucleoside chemistry; protecting groups; RNA synthesis; Sonogashira reaction; Introduction Oligoribonucleotides

Electrophilic oligodeoxynucleotide synthesis using dM-Dmoc for amino protection

• Shahien Shahsavari,
• Dhananjani N. A. M. Eriyagama,
• Bhaskar Halami,
• Vagarshak Begoyan,
• Marina Tanasova,
• Jinsen Chen and
• Shiyue Fang

Beilstein J. Org. Chem. 2019, 15, 1116–1128, doi:10.3762/bjoc.15.108

• function in linker 4 after oxidation under nearly neutral conditions is also important for considering using the technology for oligoribonucleotides (ORNs) synthesis. One potential problem to use the technology for ORN synthesis is that during oxidation of the Dmoc and dM-Dmoc functions using sodium

Synthesis of oligonucleotides on a soluble support

• Harri Lönnberg

Beilstein J. Org. Chem. 2017, 13, 1368–1387, doi:10.3762/bjoc.13.134

• Scheme 1). Compared to oligodeoxyribonucleotides (ODNs), the synthesis of oligoribonucleotides (ORNs) is complicated by the presence of an additional nucleophilic functionality, viz. the 2´-OH that has to be kept protected as long as basic conditions are required during synthesis and deprotection of the

• removed by simple extraction with DCM. A pentameric oligonucleotide, 5´-TACTT-3´, was obtained in 52% yield on using 1.5 equiv of phosphoramidites and 1.5 equiv of DCI as an activator. Synthesis of oligoribonucleotides by the phosphoramidite chemistry Three different protocols, all based on separation of

• the support-bound oligonucleotide from low-molecular weight compounds by precipitation, have been utilized for the synthesis of oligoribonucleotides by phosphoramidite chemistry. A highly hydrophobic support that is well soluble in THF, CHCl3 and DCM, but insoluble in MeOH, MeCN and EtCN, has been

Facile synthesis of a 3-deazaadenosine phosphoramidite for RNA solid-phase synthesis

• Elisabeth Mairhofer,
• Elisabeth Fuchs and
• Ronald Micura

Beilstein J. Org. Chem. 2016, 12, 2556–2562, doi:10.3762/bjoc.12.250

• mechanisms. Therefore, 1-deazaadenosine (c1A), 1-deaza-2’-deoxyadenosine (c1dA), 3-deazaadenosine (c3A), and 3-deaza-2’-deoxyadenosine (c3dA), and the corresponding phosphoramidites to prepare oligoribonucleotides are highly requested nucleoside modifications. Unfortunately, synthetic approaches to achieve

Solution phase synthesis of short oligoribonucleotides on a precipitative tetrapodal support

• Alejandro Gimenez Molina,
• Amit M. Jabgunde,
• Pasi Virta and
• Harri Lönnberg

Beilstein J. Org. Chem. 2014, 10, 2279–2285, doi:10.3762/bjoc.10.237

• Alejandro Gimenez Molina Amit M. Jabgunde Pasi Virta Harri Lonnberg Department of Chemistry, Faculty of Mathematics and Natural Sciences, University of Turku, FI-20014, Turku, Finland 10.3762/bjoc.10.237 Abstract An effective method for the synthesis of short oligoribonucleotides in solution has

• in high yields. Keywords: nucleic acids; oligoribonucleotides; phosphoramidite; soluble support; synthesis; Introduction Recognition of short noncoding RNAs as regulatory elements of gene expression [1][2][3][4][5] has attracted interest in their physico-chemical properties, including structure

• second after the 5'-deprotection. Owing to the symmetrical tetrapodal structure of the support, the completeness of couplings may be verified by 1H NMR spectroscopy. We now report on the synthesis of short oligoribonucleotides on this support. Unfortunately, commercially available building blocks that

Multicomponent synthesis of artificial nucleases and their RNase and DNase activity

• Anton V. Gulevich,
• Lyudmila S. Koroleva,
• Olga V. Morozova,
• Valentina N. Bakhvalova,
• Vladimir N. Silnikov and
• Valentine G. Nenajdenko

Beilstein J. Org. Chem. 2011, 7, 1135–1140, doi:10.3762/bjoc.7.131

• oligoribonucleotides and an HIV-1 recombinant RNA fragment 96 nucleotides long [17]. Previously, compounds 1 and 2 have been synthesized from the corresponding diamines by condensation with protected natural amino acids and subsequent deprotection [18]. This approach is significantly limited by using available natural