Boron-containing nucleic acids. 2. Synthesis of oligodeoxynucleoside boranophosphates

Hybridization Studies with Chiral Peptide Nucleic Acids

“…The difference in T m s of cPNAs 2 and 4 is more pronounced when they are hybridized with oligodeoxynucleotides in accord with theory (25). Thus with the oligonucleotide (dA) 10 , cPNA 2 gave a T m of 61ЊC, whereas the cPNA 4 gave a broader melting curve with a T m of approximately 42ЊC. These observations suggest that where the opportunity for cooperative binding does not exist then the cPNA 2 does bind more effectively than cPNA 4 to a complementary oligonucleotide sequence.…”

Synthesis and Evaluation of Modified Oligodeoxynucleotides Containing Diphosphodiester Internucleotide Linkages

“…[1][2][3][4][5] To a great extent, these modifications have focused on replacing the phosphodiester group by phosphodiester mimics, such as phosphorothioate, [6] methylphosphate, [7] phosphoramidates, [8] boranophosphate, [9] alkylphosphotriesters, [10] phosphorodithioate, [11] phosphonomethyl, [12] propynes, [13] diene, [14] phosphonoformate, [15] and other groups. [16] The phosphate-modified ODNs have been used as inhibitors of gene expression, [1] viral enzymes, [2,3] in vitro messenger-RNA translation, [4] and sequence-specific DNA binding proteins.…”

Boron Clusters − A New Entity for DNA‐Oligonucleotide Modification

“…[70] Thus, 2Ј-and 3Ј-oxygen functionalities in the uridine 13 were activated with dibutyltin oxide yielding the intermediate 2Ј,3Ј-O,O-dibutylstannyleneuridine (14). [71] Alkylation of 14 with propargyl bromide gave a mixture of 2Ј-O-(3-prop-1-ynyl)uridine (15a) and 3Ј-O-(3-prop-1-ynyl)uridine (15b).…”