2′-O, 4′-C-ethylene-bridged nucleic acids (ENA): highly nuclease-resistant and thermodynamically stable oligonucleotides for antisense drug

K Morita, C Hasegawa, M Kaneko, S Tsutsumi… - Bioorganic & Medicinal …, 2002 - Elsevier
To develop antisense oligonucleotides, novel nucleosides, 2′-O, 4′-C-ethylene
nucleosides and their corresponding phosphoramidites, were synthesized as building …

Synthesis and properties of 2′-O-neopentyl modified oligonucleotides

G Mathis, S Bourg, S Aci-Sèche, JC Truffert… - Organic & …, 2013 - pubs.rsc.org
2′-O-Neopentyldeoxyuridine (Un) was synthesized and incorporated into a series of
oligodeoxyribonucleotides. Single and triple incorporations in various arrangements were …

2′-O, 4′-C-Ethylene-bridged nucleic acids (ENA) with nuclease-resistance and high affnity for RNA

K Morita, C Hasegawa, M Kaneko… - Nucleic acids …, 2001 - academic.oup.com
Abstract Novel nucleosides, 2′-O, 4′-C-ethylene nucleosides and their corresponding
phosphoramidites, were synthesized as building blocks for antisense oligonucleotides. The …

Synthesis and hybridizing properties of isoDNAs including 3′-O, 4′-C-ethyleneoxy-bridged 5-methyluridine derivatives

T Osawa, Y Hitomi, S Wakita, H Kim, Y Ito… - Bioorganic & Medicinal …, 2018 - Elsevier
Abstract 3′, 4′-Ethyleneoxy-bridged 5-methyluridine derivatives with methyl groups in the
bridge,(R)-Me-3′, 4′-EoNA-T and (S)-Me-3′, 4′-EoNA-T, were synthesized, and these …

Site-specific incorporation of the 1-hexanol-1, N6-etheno-2′-deoxyadenosine adduct into oligodeoxyribonucleotides

VM Carvalho, D Gasparutto, P Di Mascio… - Bioorganic & medicinal …, 2003 - Elsevier
Modified oligonucleotides that contain the hydrophobic 1-hexanol-1, N6-etheno-2′-
deoxyadenosine adduct have been synthesized using a mild solid phase phosphoramidite …

Oligonucleosides with a Nucleobase‐Including Backbone. Part 12: Synthesis of Mixed Ethynylene‐Linked Uridine‐and Adenosine‐Derived Tetramers

S Eppacher, PK Bhardwaj, B Bernet… - Helvetica chimica …, 2004 - Wiley Online Library
In contradistinction to the corresponding Grignard reagent, bis [(trimethylsilyl) ethynyl] zinc
reacted with the 5′‐oxoadenosine 3 diastereoselectively to the β‐d‐allo‐hept‐6 …

Nucleosides and Nucleotides. 170. Synthesis and Properties of Oligodeoxynucleotides Containing 5-[N-[2-[N, N-Bis (2-aminoethyl)-amino] ethyl] carbamoyl]-2 ' …

Y Ueno, M Mikawa, A Matsuda - Bioconjugate chemistry, 1998 - ACS Publications
The synthesis of oligodeoxynucleotides (ODNs) containing 5-[N-[2-[N, N-bis (2-aminoethyl)
amino] ethyl] carbamoyl]-2 '-deoxyuridine (BA E) and 5-[N-[3-[N, N-bis (3-aminopropyl) …

Synthesis and Characterization of 8-Methoxy-2′-Deoxyadenosine-Containing Oligonucleotides to Probe the Syn Glycosidic Conformation of 2′-deoxyadenosine …

RG Eason, DM Burkhardt, SJ Phillips… - Nucleic acids …, 1996 - academic.oup.com
Abstract The synthesis of 8-methoxy-2′-deoxyadenosine (moA) protected at N6 as an N, N-
dimethylformamidine derivative and incorporation of the modified nucleoside into …

N,N′-Bis-(2-(cyano)ethoxycarbonyl)-2-methyl-2-thiopseudourea: A Guanylating Reagent for Synthesis of 2′-O-[2-(Guanidinium)ethyl]-Modified Oligonucleotides

TP Prakash, A Püschl, M Manoharan - … , Nucleotides, and Nucleic …, 2007 - Taylor & Francis
A guanylating reagent, N, N′-bis-(2-(cyano) ethoxycarbonyl)-2-thiopseudourea, was
synthesized and used for synthesis of 2′-O-[2-(guanidinium) ethyl](2′-O-GE) modified …

2′-C,4′-C-Ethyleneoxy-Bridged 2′-Deoxyribonucleic Acids (EoDNAs) with Thymine Nucleobases: Synthesis, Duplex-Forming Ability, and Enzymatic Stability

T Osawa, S Obika, Y Hari - Non-Natural Nucleic Acids: Methods and …, 2019 - Springer
This chapter describes procedures for (1) the synthesis of six 2′-C, 4′-C-ethyleneoxy-
bridged thymidine phosphoramidites, ie, methylene-EoDNA-T,(R)-Me-methylene-EoDNA …