Synthesis and Properties of 2′-O,4′-C-Ethyleneoxy Bridged 5-Methyluridine

Y Hari, T Morikawa, T Osawa, S Obika - Organic letters, 2013 - ACS Publications
2′-O, 4′-C-Ethyleneoxy bridged 5-methyluridine (EoNA-T), possessing a seven-
membered linkage and an anomeric 4′-carbon, was synthesized and introduced into …

Synthesis and Properties of Oligonucleotides Containing 2′-O,4′-C-Methyleneoxy-Bridged Pyrimidine Derivatives

M Shoji, Y Fuchi, T Osawa, H Kim, Y Ito… - The Journal of Organic …, 2022 - ACS Publications
In this study, 2′-O, 4′-C-methyleneoxy-bridged nucleic acid, a unique consecutive three-
acetal-containing nucleic acid (TaNA), was designed. Pyrimidine derivatives of methylated …

[HTML][HTML] Synthesis of Oligonucleotides Containing 2′-N-alkylaminocarbonyl-2′-amino-LNA (2′-urea-LNA) Moieties Using Post-Synthetic Modification Strategy

S Yamashita, K Nishida, T Osawa, A Nakanishi, Y Ito… - Molecules, 2020 - mdpi.com
The post-synthetic modification of an oligonucleotide is a powerful strategy for the synthesis
of various analogs of the oligonucleotide, aiming to achieve the desired functions. In this …

Preparation and properties of 2′, 5′-linked oligonucleotide analogues containing 3′-O, 4′-C-methyleneribonucleosides

S Obika, K Morio, Y Hari, T Imanishi - Bioorganic & medicinal chemistry …, 1999 - Elsevier
Bicyclic nucleoside analogues, 3′-O, 4′-C-methyleneuridine and-5-methyluridine, were
successfully incorporated into oligonucleotides via connection with 2′, 5′-phosphodiester …

Synthesis and Properties of the 5-Methyluridine Derivative of 3,4-Dihydro-2H-pyran-Bridged Nucleic Acid (DpNA)

T Osawa, Y Hari, M Dohi, Y Matsuda… - The Journal of Organic …, 2015 - ACS Publications
A novel 2′-O, 4′-C-bridged nucleic acid, 3, 4-dihydro-2 H-pyran bridge moiety (DpNA),
with a dioxabicyclo [3.2. 1] oct-3-ene ring was designed. Construction of the dihydropyran …

Synthesis and properties of triplex-forming oligonucleotides containing 2′-O-(2-methoxyethyl)-5-(3-aminoprop-1-ynyl)-uridine

C Lou, Q Xiao, L Brennan, ME Light… - Bioorganic & medicinal …, 2010 - Elsevier
2′-O-(2-Methoxyethyl)-5-(3-aminoprop-1-ynyl)-uridine phosphoramidite (MEPU) has been
synthesized from d-ribose and 5-iodouracil and incorporated into triplex-forming …

Synthesis, duplex-forming ability, enzymatic stability, and in vitro antisense potency of oligonucleotides including 2′-C, 4′-C-ethyleneoxy-bridged thymidine …

T Osawa, M Sawamura, F Wada… - Organic & …, 2017 - pubs.rsc.org
We synthesized thymidine derivatives of 2′-C, 4′-C-ethyleneoxy-bridged 2′-
deoxyribonucleic acids with an 8′-methyl group ((R)-Me-EoDNA and (S)-Me-EoDNA) and …

Synthesis of the Methyl Analog of 2′-O,4′-C-Ethylene-Bridged 5-Methyluridine via Intramolecular Radical Cyclization and Properties of Modified Oligonucleotides

Y Ito, N Tsutsui, T Osawa, Y Hari - The Journal of Organic …, 2019 - ACS Publications
The synthesis of 6′ S-Me-2′-O, 4′-C-ethylene-bridged 5-methyluridine (6′ S-Me-ENA-
T) was achieved using visible light-mediated stereoselective radical cyclization as a key …

Synthesis and properties of novel 2′-C, 4′-C-ethyleneoxy-bridged 2′-deoxyribonucleic acids with exocyclic methylene groups

T Osawa, S Obika, Y Hari - Organic & Biomolecular Chemistry, 2016 - pubs.rsc.org
Three 2′-C, 4′-C-ethyleneoxy-bridged 2′-deoxyribonucleic acids possessing six-
membered bridges with 6′-oxygen and 8′-exocyclic methylene groups (methylene …

A New Route to 2'-O-Alkyl-2-thiouridine Derivatives via 4-O-Protection of the Uracil Base and Hybridization Properties of Oligonucleotides Incorporating These …

I Okamoto, K Shohda, K Seio… - The Journal of Organic …, 2003 - ACS Publications
Oligonucleotides containing 2-thiouridine (s2U) in place of uridine form stable RNA
duplexes with complementary RNAs. Particularly, this modified nucleoside has proved to …