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Modified ONs were synthesized on a standard succinyl-linker solid support with a DNA synthesizer using 2?-O-AcSM phosphoramidites 1a-d and commercially available 2?-O-pivaloyloxymethyl (PivOM) ribonucleoside phosphoramidites as 2?OH precursors. The ON elongation was performed on a 1 ?mol scale with a 180 s coupling step according to the RNA synthesis method previously developed by us (Scheme 1). 28 Following the assembly, the cyclization was performed with 20 equivalents of 2?,2?-dithiopyridine in an anhydrous butylamine/THF (5 : 95) solution for 30 min. During this reaction, cyanoethyl groups were also removed. Then, an ammonia treatment removed the acyl protecting groups from the nucleobases, 2?-O-PivOM groups and released ON from the solid support. Crude ONs were purified by ion-exchange high-performance liquid chromatography (IEX-HPLC). The low yields (range from 1.4% to 7.0%) might be explained by the premature release of a part of the oligonucleotide from solid support during the butylamine treatment (Table 1). The presence of the S-S bridge was ascertained by MALDI-TOF mass spectrometry (Table 1 and ESI, Fig. S13-S23 ?). A difference of 90.5 was calculated between the m/z of Fig. 1 (A) Hairpin models containing 4 (H4) or 5 (H5) uridines in the loop portion. The disulfide bridge was introduced at four different positions, Results and discussion Synthesis of oligoribonucleotides modified by a 2?,2?-S-S bridge The formation of the S-S bridge between two 2?-O-AcSM adjacent nucleotides results in an intramolecular thiol-disulfide exchange reaction between a thiolate, vol.2 ,
, The following HPLC solvent systems were used: 5 or 20% CH 3 CN in 25 mM Tris-HCl buffer, pH 8 (buffer A) and 20% CH 3 CN containing 200 mM NaClO 4 in 25 mM Tris-HCl buffer, pH 8 or 5% CH 3 CN containing 400 mM NaClO 4 in 25 mM Tris-HCl buffer, pH 8 (buffer B). Flow rates were 1.0 mL min ?1 and 4 mL min ?1 for analysis and semipreparative purposes, respectively; UV detection was performed at 260 nm. MALDI-TOF mass spectra were recorded using a Voyager-DE spectrometer equipped with an N 2 laser (337 nm) (PerSeptive Biosystems, USA) or an Axima Assurance spectrometer equipped with an N 2 laser (337 nm) (Shimadzu Biotech) using 2,4,6-trihydroxyacetophenone as a saturated solution in a mixture of acetonitrile/0.1 M ammonium citrate solution (1 : 1, v/v) for the matrix. Analytical samples were mixed with the matrix in the 1 : 5 (v/v) ratio, crystallized on a 100-well or 384-well stainless-steel plate and analyzed, DNAPac PA 100 columns (4 × 250 mm for analysis or 9 × 250 mm, Dionex)
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