Intraduplex Photo-cross-linking of p-Azidoaniline Residue and Amino Acid Side Chains Linked to the Complementary Oligonucleotides via a New Phosphorylating Intermediate Formed in the Mukaiyama System

Oligonucleotide—Minor Groove Binder 1:2 Conjugates: Side by Side Parallel Minor Groove Binder Motif in Stabilization of DNA Duplex

“…[27,29,30] The phosphate activation step was done in organic solvent (DMSO) and the attachment of the ligand in water-DMSO mixture.…”

Synthesis and Molecular Modeling Studies of Fullerene−5,6,7-Trimethoxyindole−Oligonucleotide Conjugates as Possible Probes for Study of Photochemical Reactions in DNA Triple Helices

“…The conjugates between fullerene derivatives 14, 24, and 26 and the 5Ј-phosphorylated oligonucleotide pTTTTC* TTTTC*C*C*C*C*C*T (where C* is 5-methylcytosine, to facilitate the protonation of the cytidine moiety necessary for triplex formation) were synthesized by a previously reported general synthetic strategy, [21,22] summarized in Scheme 5. The terminal phosphate oligonucleotide (16-mer) 27 was activated (28) by means of Mukaiyama reagents: [23,24] triphenylphosphaneϪdipyridyl 2,2Ј-disulfide in the presence of 4-(dimethylamino)pyridine, precipitated by 10 vol-equiv.…”

Design and Synthesis of Metal-Free Artificial Ribonucleases

“…The terminal phosphate groups of oligonucleotides (0.2 μmol) were activated by triphenylphosphine (10 μmol) and 2,2'-dipyridyl disulfide (10 μmol) in the presence of Nmethylimidazole (MeIm) or 4-dimethylaminopyridine (DMAP) at RT for 10 min, and compound 36 or 37 (30 μmol) was added to the activated oligonucleotide solution and incubated at RT for 2 h. ODN-conjugates were precipitated by 2 % LiClO 4 in acetone and purified by RP-HPLC. Using histamine as an example, we have demonstrated [48] that the introduction of a protective group into the imidazole ring is unnecessary, and the resulting reactive derivative reacts predominantly with an aliphatic amino group (Scheme 1).…”