181999-83-7Relevant academic research and scientific papers
Synthesis and Properties of Oligonucleotides Having Ethynylphosphonate Linkages
Horiba, Masahiko,Obika, Satoshi,Yamaguchi, Takao
, (2020)
Ethynylphosphonate (EP)-linked thymidine dimers were synthesized via a palladium-catalyzed cross-coupling reaction and successfully incorporated into oligonucleotides. The oligonucleotides containing EP linkages appropriately formed a duplex with their complementary single-stranded RNA (ssRNA) and single-stranded DNA. The oligonucleotides containing both the EP linkages and 2′-O,4′-C-methylene-bridged nucleic acid/locked nucleic acid exhibited strong duplex-forming ability toward the complementary ssRNA. The EP-modified oligonucleotides exhibited higher exonuclease resistances than their natural counterparts. Moreover, one EP modification to a gapmer-type antisense oligonucleotide resulted in a switch of the cleavage site in the target ssRNA. Therefore, the EP modification can be applied for controlling the cleavage site in the RNase H-dependent mechanism.
Synthesis and hybridization data of oligonucleotide analogs with triazole internucleotide linkages, potential antiviral and antitumor agents
Varizhuk, Anna,Chizhov, Alexandr,Florentiev, Vladimir
experimental part, p. 127 - 131 (2011/07/08)
Triazolyl-functionalized oligonucleotide (ON) analogs have received much attention as potential antitumor and antiviral agents. The most promising of such analogs are those exhibiting high binding affinity toward native DNA/RNA, since they may prove to be
Commercially available 5'-DMT phosphoramidites as reagents for the synthesis of vinylphosphonate-linked oligonucleic acids.
Abbas,Bertram,Hayes
, p. 3365 - 3367 (2007/10/03)
[reaction: see text]. Commercially available cyanoethyl phosphoramidites derived from T, d(C), d(A), and d(G) were hydrolyzed (1H-tetrazole, MeCN/H2O) to give the corresponding H-phosphonates in excellent yields. Palladium(0)-catalyzed cross-coupling of e
A novel palladium-catalysed coupling strategy for the rapid synthesis of nucleic acid analogues bearing modified backbones
Abbas, Sahar,Hayes, Christopher J.
, p. 1124 - 1126 (2007/10/03)
The synthesis of a 5'-deoxy-5'-methylidene phosphonate-containing thymidine dimer 14 has been achieved using a palladium-catalysed cross coupling reaction as a key step. The E-vinyl bromide 9 was synthesised from the corresponding 1,1-dibro-moolefin 7 via
