1226528-07-9Relevant academic research and scientific papers
Synthesis of triazole-linked homonucleoside polymers through topochemical azide-alkyne cycloaddition
Pathigoolla, Atchutarao,Sureshan, Kana M.
, p. 9522 - 9525 (2014)
There is a great deal of interest in developing stable modified nucleic acids for application in diverse fields. Phosphate-modified DNA analogues, in which the phosphodiester group is replaced with a surrogate group, are attractive because of their high stability and resistance to nucleases. However, the scope of conventional solution or solid-phase DNA synthesis is limited for making DNA analogues with unnatural linkages. Other limitations associated with conventional synthesis include difficulty in making larger polymers, poor yield, incomplete reaction, and difficult purification. To circumvent these problems, a single-crystal-to-single-crystal (SCSC) synthesis of a 1,5-triazole-linked polymeric ssDNA analogue from a modified nucleoside through topochemical azide-alkyne cycloaddition (TAAC) is reported. This is the first solvent-free, catalyst-free synthesis of a DNA analogue that proceeds in quantitative yield and does not require any purification. Crystals go click: Modified DNA analogues are attractive materials for applications in many fields, however, the synthesis of DNA analogues by conventional methods is difficult owing to poor yield and efficiency and tedious purification. A highly homogeneous, enzyme-stable, crystalline ssDNA analogue was synthesized regiospecifically in quantitative yield through single-crystal-to-single-crystal azide-alkyne cycloaddition polymerization of a modified nucleoside.
Synthesis and structures of deoxyribonucleoside analogues for triazole-linked DNA (TLDNA)
Fujino, Tomoko,Tsunaka, Nobuhide,Guillot-Nieckowski, Marine,Nakanishi, Waka,Iwamoto, Takeaki,Nakamura, Eiichi,Isobe, Hiroyuki
supporting information; experimental part, p. 2036 - 2038 (2010/06/14)
Deoxyribonucleoside analogues bearing acetylene group at the pseudo-5′-position and azido group at the pseudo-3′-position have been synthesized by transglycosylation reaction of deoxythymidine analogue with adenine, cytosine, and guanine nucleobases as nu
