239808-67-4Relevant academic research and scientific papers
Synthesis and thermal stabilities of oligonucleotides containing 2′-: O,4′- C -methylene bridged nucleic acid with a phenoxazine base
Kishimoto, Yuki,Fujii, Akane,Nakagawa, Osamu,Nagata, Tetsuya,Yokota, Takanori,Hari, Yoshiyuki,Obika, Satoshi
, p. 8145 - 8152 (2017)
We designed and synthesized a novel artificial 2′-O,4′-C-methylene bridged nucleic acid (2′,4′-BNA/LNA) with a phenoxazine nucleobase and named this compound BNAP. Oligodeoxynucleotide (ODN) containing BNAP showed higher binding affinities toward compleme
2′,4′-BNA/LNA with 9-(2-Aminoethoxy)-1,3-diaza-2-oxophenoxazine Efficiently Forms Duplexes and Has Enhanced Enzymatic Resistance**
Kishimoto, Yuki,Nakagawa, Osamu,Fujii, Akane,Yoshioka, Kotaro,Nagata, Tetsuya,Yokota, Takanori,Hari, Yoshiyuki,Obika, Satoshi
, p. 2427 - 2438 (2021)
Artificial nucleic acids are widely used in various technologies, such as nucleic acid therapeutics and DNA nanotechnologies requiring excellent duplex-forming abilities and enhanced nuclease resistance. 2′-O,4′-C-Methylene-bridged nucleic acid/locked nuc
Synthesis and evaluation of artificial nucleic acid bearing an oxanorbornane scaffold
Aoyama, Hiroshi,Ishida, Kenta,Kasahara, Yuuya,Komine, Hibiki,Mori, Shohei,Morihiro, Kunihiko,Obika, Satoshi,Okuda, Takumi,Yamaguchi, Takao
, (2020)
Natural oligonucleotides have many rotatable single bonds, and thus their structures are inherently flexible. Structural flexibility leads to an entropic loss when unwound oligonucleotides form a duplex with single-stranded DNA or RNA. An effective approa
6′-Fluoro[4.3.0]bicyclo nucleic acid: Synthesis, biophysical properties and molecular dynamics simulations
Frei, Sibylle,Istrate, Andrei,Leumann, Christian J.
, p. 3088 - 3097 (2018)
Here we report on the synthesis, biophysical properties and molecular modeling of oligonucleotides containing unsaturated 6'-fluoro[4.3.0]bicyclo nucleotides (6'F-bc4,3-DNA). Two 6'F-bc4,3 phosphoramidite building blocks (T and C) were synthesized startin
Base-resolution analysis of 5-hydroxymethylcytidine by selective oxidation and reverse transcription arrest
Aburatani, Hiroyuki,Hayashi, Gosuke,Koyama, Kenta,Nagae, Genta,Okamoto, Akimitsu,Ota, Satoshi,Ueda, Hiroki
, p. 6478 - 6486 (2021/08/03)
While 5-hydroxymethylcytidine in RNA (hm5C) is associated with cellular development and differentiation, its distribution and biological function remain largely unexplored because suitable detection methods are lacking. Here, we report a base-r
Access to 1′-Amino Carbocyclic Phosphoramidite to Enable Postsynthetic Functionalization of Oligonucleotides
Rydzik, Anna M.,Balk, Regina,Koegler, Martin,Steinle, Tobias,Riether, Doris,Gottschling, Dirk
supporting information, p. 6735 - 6739 (2021/09/11)
We report a synthesis of a carbocyclic, abasic RNA phosphoramidite decorated with an amino functionality. The building block was efficiently incorporated into an RNA oligonucleotide in a site-specific manner, followed by deprotection to a free amino group
Synthesis of the 5-methyluridine monomer of 3-O,4-C-ethyleneoxy-bridged nucleic acid
Osawa, Takashi,Dohi, Masakazu,Hitomi, Yuka,Ito, Yuta,Obika, Satoshi,Hari, Yoshiyuki
, p. 342 - 352 (2019/05/16)
– A novel bridged nucleic acid, 3-O,4-C-ethyleneoxy-bridged nucleic acid (3,4-EoNA), forming 2,5-linkage with the flanking nucleotides in oligonucleotides was designed. The 3,4-EoNA is expected to improve the biophysical properties of the oligonucleotides
Synthesis and properties of 2'-deoxy-trans-3'4'-BNA with S-type sugar puckering
Kodama, Tetsuya,Sugaya, Kensaku,Harada, Yasuki,Mitsuoka, Yasunori,Imanishi, Takeshi,Obika, Satoshi
experimental part, p. 1209 - 1217 (2010/10/20)
2'-deoxy-trans-3',4'-BNA monomer, which was previous synthesized as part of a study on bridged nucleic acids with S-type sugar puckering, was introduced into an oligodeoxynucleotide using phosphoramidite chemistry, and the hybridization ability of the 2'-
Synthesis and properties of trans-3′,4′-bridged nucleic acids having typical S-type sugar conformation
Sekiguchi, Mitsuaki,Obika, Satoshi,Harada, Yasuki,Osaki, Tomohisa,Somjing, Roongjang,Mitsuoka, Yasunori,Shibata, Nao,Masaki, Miyuki,Imanishi, Takeshi
, p. 1306 - 1316 (2007/10/03)
The synthesis of nucleoside analogues with a conformationally restricted sugar moiety is of great interest. The present research describes the synthesis of BNA (bridged nucleic acid) monomers 1 and 2 bearing a 4,7-dioxabicyclo[4.3.0] nonane skeleton and a methoxy group at the C2' position. Conformational analysis showed that the sugar moiety of these monomers is restricted in a typical S-type conformation. It was difficult to synthesize the phosphoramidite derivative of the ribo-type monomer 1, while the phosphoramidite of the arabino-type monomer 2 was successfully prepared and incorporated into oligodeoxynucleotides (ODNs). The hybridization ability of the obtained ODN derivatives containing 2 with complementary strands was evaluated by melting temperature (Tm) measurements. As a result, the ODN derivatives hybridized with DNA and RNA complements in a sequence-selective manner, though the stability of the duplexes was lower than that of the corresponding natural DNA/DNA or DNA/RNA duplex.
