Publications
2024年
原著論文
Synthesis and characterization of oligonucleotides containing 2'-O,4'-C-methyleneoxy-bridged 5-methyluridine with an unsubstituted bridge
Misa Shoji, Yasufumi Fuchi, Yuta Ito, Yoshiyuki Hari*
Tetrahedron 2024, 163, 134140 (doi:10.1016/j.tet.2024.134140).
Synthesis of fluorescent 5-heteroarylpyrimidine-containing oligonucleotides via post-synthetic trifluoromethyl conversion
Yuta Ito, Hisato Tanaka, Ayana Murakami, Yasufumi Fuchi, Yoshiyuki Hari*
Org. Biomol. Chem. 2024, 22, 3510-3517 (doi:10.1039/d4ob00402g).
Synthesis of a hydrophobic phenanthrene-containing universal support for solid-phase oligonucleotide synthesis
Yasufumi Fuchi, Kuria Shiota, Yoshiyuki Hari*
Curr. Protoc. (Invited) 2024, 4, e1013 (doi:10.1002/cpz1.1013).
Synthesis and properties of 2'-deoxyadenosine mimics bearing thieno[3,2-d]pyrimidine ring
Yasufumi Fuchi, Miho Kawaguchi, Yuta Ito, Yoshiyuki Hari*
Synlett (Invited) 2024, 35, 716-720 (doi:10.1055/s-0042-1751508).
総説
糖部4'位に発生する炭素ラジカルを利用した修飾ヌクレオシドの合成
伊藤 勇太
Yakugaku Zasshi (Invited) 2024, 144, 877-886 (doi:10.1248/yakushi.24-00117).
核酸合成用ユニバーサルリンカー「PTリンカー」
張 功幸
和光純薬時報 (Invited) 2024, 92, 2-4.
和書
高性能アンチジーン核酸の特徴とその合成 (第2章第3節)
張 功幸
核酸医薬 ～モダリティ・合成・分析・DDSの最新動向～, エヌ・ティー・エス, 83-95 (2024) (ISBN:978-4-86043-886-9).
2023年
原著論文
Chemical conversion of 5-fluoromethyl- and 5-difluoromethyl-uracil bases in oligonucleotides using postsynthetic modification strategy
Yuta Ito, Chisa Takemori, Yoshiyuki Hari*
Curr. Protoc. Nucleic Acid Chem. (Invited) 2023, 3, e837 (doi:10.1002/cpz1.837).
Development and crosslinking properties of psoralen-conjugated triplex-forming oligonucleotides as antigene tools targeting genome DNA
Yu Mikame, Honoka Eshima, Haruki Toyama, Juki Nakao, Misaki Matsuo, Tsuyoshi Yamamoto, Yoshiyuki Hari, Jun A. Komano, Asako Yamayoshi*
ChemMedChem 2023, 18, e202300348 (doi:10.1002/cmdc.202300348).
Synthesis of purine derivatives of Me-TaNA and properties of Me-TaNA-modified oligonucleotides
Yasufumi Fuchi, Kouki Watanabe, Misa Shoji, Yuta Ito, Yoshiyuki Hari*
Org. Biomol. Chem. 2023, 21, 5203-5213 (doi:10.1039/d3ob00745f).
Expansion of phosphoramidite chemistry in solid-phase oligonucleotide synthesis: Rapid 3'-dephosphorylation and strand cleavage
Kazuki Yamamoto, Yasufumi Fuchi, Yuta Ito, Yoshiyuki Hari*
J. Org. Chem. 2023, 88, 2726-2734 (doi:10.1021/acs.joc.2c02195).
Benzo-fused 7-oxabicyclo[2.2.1]heptane-2,3-diol derivatives as universal linkers for solid-phase oligonucleotide synthesis
Yasufumi Fuchi, Kazuki Yamamoto, Yuta Ito, Yoshiyuki Hari*
Synthesis 2023, 55, 1112-1122 (doi:10.1055/s-0042-1751405).
2022年
原著論文
Generation of 4ʹ-carbon radicals via 1,5-hydrogen atom transfer for the synthesis of bridged nucleosides
Yuta Ito, Koichi Mizuno, Sanae Sumise, Airi Kimura, Nozomi Noguchi, Yasufumi Fuchi, Yoshiyuki Hari*
Org. Lett. 2022, 24, 7696-7700 (doi:10.1021/acs.orglett.2c03285).
Synthesis and properties of oligonucleotides containing 2ʹ-O,4ʹ-C-methyleneoxy-bridged pyrimidine derivatives
Misa Shoji, Yasufumi Fuchi, Takashi Osawa, Han Kim, Yuta Ito, Yoshiyuki Hari*
J. Org. Chem. 2022, 87, 11743-11750 (doi:10.1021/acs.joc.2c01409).
総説
Synthesis of nucleobase-modified oligonucleotides by post-synthetic modification in solution
Yuta Ito, Yoshiyuki Hari*
Chem. Rec. (Invited) 2022, 22, e202100325 (doi:10.1002/tcr.202100325).
2021年
原著論文
New cleavable spacers for tandem synthesis of multiple oligonucleotides
Kazuki Yamamoto, Yasufumi Fuchi, Masaya Okabe, Takashi Osawa, Yuta Ito, Yoshiyuki Hari*
Synthesis 2021, 53, 4440-4448 (doi:10.1055/a-1538-9883).
Synthesis and properties of oligonucleotides containing 2ʹ-O,4ʹ-C-ethylene-bridged 5-methyluridine with exocyclic methylene and methyl groups in the bridge
Yuta Ito, Kodai Nishida, Norika Tsutsui, Yasufumi Fuchi, Yoshiyuki Hari*
Eur. J. Org. Chem. 2021, 2021, 4993-5002 (doi:10.1002/ejoc.202100947).
Bicyclo[2.2.2]octane-2,3-diol as a universal linker for the solid-phase
synthesis of oligonucleotides
Kazuki Yamamoto, Yasufumi Fuchi, Yuta Ito, Yoshiyuki Hari*
Tetrahedron 2021, 92, 132261 (doi:10.1016/j.tet.2021.132261).
Synthesis and properties of oligonucleotides bearing thymidine derivatives with 1,6-dioxaspiro[4.5]decane skeleton
Takashi Osawa, Miho Kawaguchi, Ye-Jin Jang, Yuta Ito, Yoshiyuki Hari*
Bioorg. Med. Chem. 2021, 31, 115966 (doi:10.1016/j.bmc.2020.115966).
Post-synthetic modification of oligonucleotides containing 5-mono- and 5-di-fluoromethyluridines
Yuta Ito, Honoka Hayashi, Yasufumi Fuchi, Yoshiyuki Hari*
Tetrahedron 2021, 77, 131769 (doi:10.1016/j.tet.2020.131769).
2ʹ,4ʹ-BNA/LNA with 9-(2-aminoethoxy)-1,3-diaza-2-oxophenoxazine efficiently forms duplexes and has enhanced enzymatic resistance
Yuki Kishimoto, Osamu Nakagawa*, Akane Fujii, Kotaro Yoshioka, Tetsuya Nagata, Takanori Yokota, Yoshiyuki Hari, Satoshi Obika*
Chem. Eur. J. 2021, 27, 2427-2438 (doi:10.1002/chem.202003982).
The effect of base triplets adjacent to a T•CG or 5-methylC•CG triplet in the triplex DNA
Yuta Ito, Chisa Hama, Takashi Osawa, Yoshiyuki Hari*
Heterocycles (Invited) 2021, 103, 322-330 (doi:10.3987/COM-20-S(K)16).
2020年
原著論文
Synthesis and hybridization properties of iridium(III) polypyridyl complex-conjugated oligonucleotide
Yuta Ito, Koichi Mizuno, Kohei Domoto, Yoshiyuki Hari*
Nucleos. Nucleot. Nucleic Acids (Invited) 2020, 39, 69-81 (doi:10.1080/15257770.2019.1690150).
Synthesis of oligonucleotides containing 2ʹ-N-alkylaminocarbonyl-2'-amino-LNA (2'-urea-LNA) moieties using post-synthetic
modification strategy
Shoko Yamashita, Kodai Nishida, Takashi Osawa, Ayumi Nakanishi, Yuta Ito, Yoshiyuki Hari*
Molecules (Invited) 2020, 25, 346 (doi:10.3390/molecules25020346).
Synthesis and hybridizing property of oligonucleotides including 2ʹ-C,4ʹ-C-ethyleneoxy-bridged 2ʹ-deoxyadenosine with an exocyclic methylene unit
Takashi Osawa, Yoshinori Onishi, Sawako Wakita, Yuta Ito, Yoshiyuki Hari*
Heterocycles (Invited) 2020, 101, 284-297 (doi:10.3987/COM-19-S(F)24).
総説
ルテニウム錯体をコンジュゲートした機能性オリゴ核酸の開発
伊藤 勇太*
有機合成化学協会誌 2020, 78, 898-900 (doi:10.5059/yukigoseikyokaishi.78.898).
Bridged nucleosides as building blocks of oligonucleotides: Synthesis and properties
Yoshiyuki Hari*
Heterocycles (Invited) 2020, 100, 681-717 (doi:10.3987/REV-19-922).
和書
アンチジーン (第Ⅱ部核酸科学の最前線)
張 功幸
核酸科学ハンドブック, 日本核酸化学会(監修), 講談社, 504-507 (2020) (ISBN:978-4-06-520786-4).
2019年
原著論文
Synthesis of 2ʹ-C,4ʹ-C-methyleneoxy-bridged thymidine derivatives and properties of modified oligonucleotides
Takashi Osawa, Han Kim, Misa Shoji, Miku Saijo, Masakazu Dohi, Yuta Ito, Satoshi Obika, Yoshiyuki Hari*
J. Org. Chem. 2019, 84, 13336-13344 (doi:10.1021/acs.joc.9b01496).
Synthesis of the methyl analog of 2ʹ-O,4ʹ-C-ethylene-bridged 5-methyluridine via intramolecular radical cyclization and properties of the modified oligonucleotides
Yuta Ito, Norika Tsutsui, Takashi Osawa, Yoshiyuki Hari*
J. Org. Chem. 2019, 84, 9093-9100 (doi:10.1021/acs.joc.9b01035).
Construction of pyrimidine bases bearing carboxylic acid equivalents at the C5 position by postsynthetic modification of oligonucleotides
Yuta Ito, Kazuki Yamamoto, Yoshiyuki Hari*
Curr. Protoc. Nucleic Acid Chem. (Invited) 2019, 78, e91 (doi:10.1002/cpnc.91).
Effective syntheses of 2',4'-BNANC monomers bearing adenine, guanine, thymine, and 5-methylcytosine, and the properties of oligonucleotides fully modified with 2',4'-BNANC
Aki Fujisaka, Yoshiyuki Hari, Hiroko Takuma, S. M. Abdur Rahman, Haruhisa Yoshikawa, Juanjuan Pang, Takeshi Imanishi, Satoshi Obika*
Bioorg. Med. Chem. 2019, 27, 1728-1741 (doi:10.1016/j.bmc.2019.02.034).
Synthesis and hybridization properties of oligonucleotides including 2'-N-alkoxycarbonyl-2'-amino-LNA derivatives
Takashi Osawa, Shoko Yamashita, Ayumi Nakanishi, Yuta Ito, Yoshiyuki Hari*
Heterocycles (Invited) 2019, 99, 502-520 (doi:10.3987/COM-18-S(F)46).
洋書
2'-C,4'-C-Ethyleneoxy-bridged 2'-deoxyribonucleic acids (EoDNAs) with thymine nucleobases:
Synthesis, duplex-forming ability and enzymatic stability
Takashi Osawa, Satoshi Obika, Yoshiyuki Hari
Non-Natural Nucleic Acids, N. Shank (ed.), Springer, 59-89 (2019).
2018年
原著論文
Post-synthetic modification of oligonucleotides containing 5-trifluoromethylpyrimidine bases
Yuta Ito, Misaki Matsuo, Kazuki Yamamoto, Wakana Yamashita, Takashi Osawa,
Yoshiyuki Hari*
Tetrahedron 2018, 74, 6854-6860 (doi:10.1016/j.tet.2018.10.006).
Photoredox-catalyzed deformylative 1,4-addition of 2'-deoxy-5'-O-phthalimidonucleosides for synthesis of 5'-carba analogs of nucleoside
5'-phosphates
Yuta Ito, Airi Kimura, Takashi Osawa, Yoshiyuki Hari*
J. Org. Chem. 2018, 83, 10701-10708 (doi:10.1021/acs.joc.8b00637).
Synthesis and properties of oligonucleotides containing 3'-O,4'-C-ethyleneoxy-bridged 5-methyluridines
Takashi Osawa, Yuka Hitomi, Sawako Wakita, Han Kim, Masakazu Dohi, Masahiko
Horiba, Yuta Ito, Satoshi Obika, Yoshiyuki Hari*
Heterocycles (Invited) 2018, 97, 306-313 (doi:10.3987/COM-18-S(T)20).
Synthesis and hybridizing properties of isoDNAs including 3'-O,4'-C-ethyleneoxy-bridged 5-methyluridine derivatives
Takashi Osawa, Yuka Hitomi, Sawako Wakita, Han Kim, Yuta Ito, Yoshiyuki Hari*
Bioorg. Med. Chem. 2018, 26, 3875-3881 (doi:10.1016/j.bmc.2018.05.043).
洋書
Site-specific modification of nucleobases in oligonucleotides
Yoshiyuki Hari
Synthesis of Therapeutic Oligonucleotides, S. Obika and M. Sekine (eds.), Springer, 131-145 (2018).
2',4'-Bridged nucleic acids containing plural heteroatoms in the bridge
moiety
Yoshiyuki Hari, Satoshi Obika
Synthesis of Therapeutic Oligonucleotides, S. Obika and M. Sekine (eds.), Springer, 201-221 (2018).
2017年
原著論文
Synthesis and thermal stabilities of oligonucleotides containing 2'-O,4'-C-methylene bridged nucleic acid with a phenoxazine base
Yuki Kishimoto, Akane Fujii, Osamu Nakagawa*, Tetsuya Nagata, Takanori Yokota, Yoshiyuki Hari, Satoshi Obika*
Org. Biomol. Chem. 2017, 15, 8145-8152 (doi:10.1039/c7ob01874f).
Triplex- and duplex-forming abilities of oligonucleotides containing 2'-deoxy-5-trifluoromethyluridine
and 2'-deoxy-5-trifluoromethylcytidine
Yuta Ito, Misaki Matsuo, Takashi Osawa, Yoshiyuki Hari*
Chem. Pharm. Bull. 2017, 65, 982-988 (doi:10.1248/cpb.c17-00530).
Synthesis, duplex-forming ability, enzymatic stability, and in vitro antisense potency of oligonucleotides including 2'-C,4'-C-ethyleneoxy-bridged thymidine derivatives
Takashi Osawa, Motoki Sawamura, Fumito Wada, Tsuyoshi Yamamoto, Satoshi Obika*, Yoshiyuki
Hari*
Org. Biomol. Chem. 2017, 15, 3955-3963 (doi:10.1039/c7ob00698e).
Synthesis of the 5-methyluridine monomer of 3'-O,4'-C-ethyleneoxy-bridged nucleic acid
Takashi Osawa, Masakazu Dohi, Yuka Hitomi, Yuta Ito, Satoshi Obika*, Yoshiyuki
Hari*
Heterocycles (Invited) 2017, 95, 342-352 (doi:10.3987/COM-16-S(S)24).
Tetrazole- and triazol-bridged nucleic acids: Synthesis, duplex stability,
nuclease resistance, and in vitro and in vivo antisense potency
Yasunori Mitsuoka, Tsuyoshi Yamamoto, Akira Kugimiya, Reiko Waki, Fumito
Wada, Saori Tahara, Motoki Sawamura, Mio Noda, Yuko Fujimura, Yuki Kato,
Yoshiyuki Hari, Satoshi Obika*
J. Org. Chem. 2017, 82, 12-24 (doi:10.1021/acs.joc.6b02417).
2016年
原著論文
Synthesis and properties of novel 2'-C,4'-C-ethyleneoxy-bridged 2'-deoxyribonucleic acids with exocyclic methylene
groups
Takashi Osawa, Satoshi Obika*, Yoshiyuki Hari*
Org. Biomol. Chem. 2016, 14, 9481-9484 (doi:10.1039/c6ob01960a).
Effect of an N-substituted in sulfonamide-bridged nucleic acid (SuNA) on
hybridization ability and duplex structure
Yasunori Mitsuoka, Hiroshi Aoyama, Akira Kugimiya, Yuko Fujimura, Tsuyoshi
Yamamoto, Reiko Waki, Fumito Wada, Saori Tahara, Motoki Sawamura, Mio Noda,
Yoshiyuki Hari, Satoshi Obika*
Org. Biomol. Chem.2016, 14, 6531-6538 (doi:10.1039/c6ob01051b).
Structure–activity relations of leucine derivatives reveal critical moieties
for cellular uptake and activation of mTORC1-mediated signaling
Shushi Nagamori, Pattama Wiriyasermkul, Suguru Okuda, Naoto Kojima, Yoshiyuki
Hari, Shigeki Kiyonaka, Yasuo Mori, Hideyuki Tominaga, Ryuichi Ohgaki,
Yoshikatsu Kanai*
Amino Acids2016, 48, 1045-1058 (doi:10.1007/s00726-015-2158-z).
総説
架橋部に複数のヘテロ原子を有する2',4'-架橋型人工核酸の合成と機能
張 功幸*, 小比賀聡*
J. Synth. Org. Chem., Jpn. (Invited) 2016, 74, 141-153 (doi:10.5059/yukigoseikyokaishi.74.141).
洋書
2’,4’-Bridged nucleic acids for targeting double-stranded DNA
Yoshiyuki Hari, Satoshi Obika
Modified Nucleic Acids, K. Nakatani and Y. Tor (eds.), Springer, 209-219 (2016).
その他
二重鎖形成能
張 功幸
J. Synth. Org. Chem., Jpn.2016, 74, 169.
2015年4月～（着任以降）
原著論文
Synthesis and properties of the 5-methyluridine derivative of 3,4-dihydro-2H-pyran-bridged nucleic acid (DpNA)
Takashi Osawa, Yoshiyuki Hari*, Masakazu Dohi, Yuya Matsuda, Satoshi Obika*
J. Org. Chem.2015, 80,10474-10481 (doi:10.1021/acs.joc.5b01425).
