Versatile synthesis of amino acid functionalized nucleosides via a domino carboxamidation reaction

• Vicky Gheerardijn,
• Jos Van den Begin and
• Annemieke Madder

Beilstein J. Org. Chem. 2014, 10, 2566–2572, doi:10.3762/bjoc.10.268

• information. Only recently, the use of synthetic oligonucleotides and their modified analogues for a range of therapeutic and diagnostic purposes [1], including antisense therapy [2][3], antigene therapy [4][5] and SNP (Single Nucleotide Polymorphism) detection [6] has gained major interest. Due to their

Molecular recognition of AT-DNA sequences by the induced CD pattern of dibenzotetraaza[14]annulene (DBTAA)–adenine derivatives

• Marijana Radić Stojković,
• Marko Škugor,
• Łukasz Dudek,
• Jarosław Grolik,
• Julita Eilmes and
• Ivo Piantanida

Beilstein J. Org. Chem. 2014, 10, 2175–2185, doi:10.3762/bjoc.10.225

• in the appearance of a strong negative band at 350 nm, characteristic for ds-DNA. This band could be used to probe the efficiency of pairing oligo dT sequences with complementary dA or rA structures, for instance, in any (antisense strategy) developed oligonucleotide, which relies on efficient and

Structure/affinity studies in the bicyclo-DNA series: Synthesis and properties of oligonucleotides containing bc^en-T and iso-tricyclo-T nucleosides

• Branislav Dugovic,
• Michael Wagner and
• Christian J. Leumann

Beilstein J. Org. Chem. 2014, 10, 1840–1847, doi:10.3762/bjoc.10.194

• ; Introduction Antisense oligonucleotides (ASOs) can interfere with gene expression via various biological mechanisms, depending on the nature of the cellular RNA target [1]. First and foremost they can inhibit translation by targeting a mature mRNA in either its coding or non-coding part of the sequence by a

Solid-phase-supported synthesis of morpholinoglycine oligonucleotide mimics

• Tatyana V. Abramova,
• Sergey S. Belov,
• Yulia V. Tarasenko and
• Vladimir N. Silnikov

Beilstein J. Org. Chem. 2014, 10, 1151–1158, doi:10.3762/bjoc.10.115

• . Keywords: labile linker; morpholino oligomers; oligonucleotide mimics; solid-phase-supported peptide synthesis (SPPS); Introduction The phosphorodiamidate morpholino oligomers (PMO) and peptide conjugated PMO (PPMO) are currently promising candidates for antisense therapy of a number of infectious and

• , methylenecarboxamide (glycine) oligomers (MorGly) (Figure 1A), being protonated at physiological pH, seem to be promising candidates for the development of novel antisense oligonucleotide mimics. A convenient synthetic procedure was previously described for protected monomers 1a–d (Figure 1B) necessary for the

• of the uracil nucleobases in the MorGly oligomers by thymines with better stacking properties may solve this problem. The synthesis of the thymine containing morpholino monomer 1e was necessary to prove this hypothesis. The promising properties of the MorGly oligomers as potential antisense agents

(Pseudo)amide-linked oligosaccharide mimetics: molecular recognition and supramolecular properties

• José L. Jiménez Blanco,
• Fernando Ortega-Caballero,
• Carmen Ortiz Mellet and
• José M. García Fernández

Beilstein J. Org. Chem. 2010, 6, No. 20, doi:10.3762/bjoc.6.20

• ,Z:Z,E equilibrium. The cavity collapses due to the presence of these intramolecular hydrogen bonds thus preventing the formation of inclusion complexes. Most examples of linear pseudoamide-linked glycooligomers correspond to oligonucleotide analogues. The “antisense” strategy to regulate gene

• [83][84]. Numerous structural analogues of DNA/RNA designed to be effective antisense/antigene agents have been reported. An interesting approach involves replacing the negatively charged phosphodiester linkages of RNA/DNA by positively charged guanidinium linkages. The guanidinium linkage is

• DNA·DNA duplexes and was able to discriminate between complementary and non-complementary base pairs. These results suggest that 52 is a good candidate for an antisense agent. A 21 base pair RNG/DNA chimera containing both anionic phosphodiester linkages of DNA and cationic guanidine linkages of RNG has