- A direct comparison of azide and nitrile vibrational probes
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The synthesis of 2′-azido-5-cyano-2′-deoxyuridine, N 3CNdU (1), from trityl-protected 2′-amino-2′-deoxyuridine was accomplished in four steps with a 12.5% overall yield. The IR absorption positions and profiles of the azide and nitrile group of
- Gai, Xin Sonia,Coutifaris, Basil A.,Brewer, Scott H.,Fenlon, Edward E.
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Read Online
- Three-pronged probes: High-affinity DNA binding with cap, β-alanines and oligopyrrolamides
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TPP oligonucleotides: Hybridization probes that interrogate target sequences through base pairing, stacking on the terminus, and binding in the minor groove are presented (see figure). All subunits of the probes contribute to the target affinity, leading
- Haug, Ruediger,Kramer, Markus,Richert, Clemens
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supporting information
p. 15822 - 15826
(2014/04/03)
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- 2′-Lipid-modified oligonucleotides via a 'Staudinger-Vilarrasa' reaction
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We report a new access to 2′-amido-2′-deoxyuridine via a Staudinger-Vilarrasa coupling reaction for the preparation of lipid-modified oligonucleotides. One or two lipidic moieties were inserted within the oligonucleotidic sequence (LONs) leading to a repertoire of original antagomir-like molecules targeting micro RNA (miRNA or miR). Melting temperature (Tm) experiments revealed that the stability of the duplexes depends on the lipid position and the number of lipid moieties inserted within the oligonucleotide sequence. Single lipid conjugations of positions 11 and 19 of LONs targeting miR-122 do not destabilize the duplexes.
- Chapuis, Hubert,Bui, Laurent,Bestel, Isabelle,Barthélémy, Philippe
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supporting information; scheme or table
p. 6838 - 6840
(2009/04/07)
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- Synthesis of functionalised nucleosides for incorporation into nucleic acid-based serine protease mimics
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The synthesis of nucleosides modified with an extra imidazole, carboxyl and hydroxyl group is described. These nucleosides can be incorporated into an oligonucleotide duplex, thus generating a novel type of serine protease mimic.
- Catry, Mieke A.,Madder, Annemieke
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p. 114 - 129
(2008/02/04)
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- Monomers for oligonucleotide synthesis with linkers carrying reactive residues: II. The synthesis of phosphoamidites on the basis of uridine and cytosine and containing a linker with methoxyoxalamide groups in position 2′
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A convenient preparative synthesis of 2′-amino-2′-deoxyuridine was developed. Starting from 2′-amino-2′-deoxyuridine and 2′-amino-2′-deoxycytidine, monomers for the phosphoamidite oligonucleotide synthesis were obtained that carry a linker with methoxyoxalamide groups in position 2′.
- Vasil'eva,Abramova,Ivanova,Shishkin,Sil'nikov
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p. 234 - 242
(2007/10/03)
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- Synthesis of Phosphoramidite Building Blocks of 2′-Amino-2′-deoxyribonucleosides: New Compounds for Oligonucleotide Synthesis
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The chemical synthesis of 2′-amino-2′-deoxyribonucleosides of uracil, cytosine, adenine, and guanine, and their conversion into suitably protected 3′-phosphoramidite building blocks 35-40 for oligonucleotide synthesis are described. The aglycone and the 2′-amino functions were protected using the 2-(4-nitrophenyl)ethoxycarbonyl (npeoc) group. The synthesis of the 3′-?-succinyl (3′-?-(3-carboxypropanoyl))-substituted starting nucleoside 41 is described and its behavior examined in solution and on solid phase with regard to an anticipated migration during 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) deprotection. Oligonucleotides were prepared using the new building blocks, and their hybridization properties were studied by UV-melting techniques.
- Greiner, Beate,Pfleiderer, Wolfgang
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p. 1528 - 1544
(2007/10/03)
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