Publications

Synthesis and Conformational Analyses of Cyclonucleoside Having 13-Membered Ring Bridging Nucleobase and 5'-Position via a Linker Containing Sulfonamide.

Kanagawa T, Tachibana S, Masaki Y, Seio K.

Org Lett. 2023 Nov 3;25(43):7868-7872. doi: 10.1021/acs.orglett.3c03094. 

Alteration of target cleavage patterns and off-target reduction of antisense Alteration of target cleavage patterns and off-target reduction of antisense oligonucleotides incorporating 2-N-carbamoyl- or (2-pyridyl)guanine.

Kanagawa T, Koyoma A, Masaki Y, Seio K.

Org Biomol Chem. 2023 Jun 28;21(25):5214-5224. doi: 10.1039/d3ob00574g.

Insertion of a methylene group into the backbone of an antisense oligonucleotide reveals the importance of deoxyribose recognition by RNase H.

Masaki Y, Tabira A, Hattori S, Wakatsuki S, Seio K.

Org. Biomol Chem. 2022 Oct 27;20:8917-8924. doi: 10.1039/D2OB01667B.

Synthesis of 2'-O-[3-(N-methylsulfamoyl)propan-1-yl]ribothymidine as a potentially applicable 2'-modified nucleoside for antisense oligonucleotides.

Tomori T, Uekusa K, Koyama A, Kanagawa T, Masaki Y, Seio K.

Bioorg Med Chem. 2022 Nov 1;73:117002. doi: 10.1016/j.bmc.2022.117002.

Quantification of synthetic errors during chemical synthesis of DNA and its suppression by non-canonical nucleosides.

Masaki Y, Onishi Y, Seio K.

Sci Rep. 2022 Jul 15;12(1):12095. doi: 10.1038/s41598-022-16222-2.

Selective and stable base pairing by alkynylated nucleosides featuring a spatially-separated recognition interface.

Okamura H, Trinh G, Dong Z, Masaki Y, Seio K, Nagatsugi F.

Nucleic Acids Res. 2022 Feb 15. doi: 10.1093/nar/gkac140.

Oligodeoxynucleotides Modified with 2'- O-(Cysteinylaminobutyl)carbamoylethylribothymidine Residues for Native Chemical Ligation with Peptide at Internal Positions.

Masaki Y, Maruyama A, Yoshida K, Tomori T, Kishimura T, Seio K.

Bioconjug. Chem. 2022 Feb 7;33(2):272-278. doi: 10.1021/acs.bioconjchem.1c00575.

Synthesis of 2′-O-alkylcarbamoylethyl-modified oligonucleotides with enhanced nuclease resistance that form isostable duplexes with complementary RNA.

Kishimura T, Tomori T, Masaki Y, Seio K.

Bioorg Med Chem Lett. 2021 Mar 1;35:127779. doi: 10.1016/j.bmcl.2021.127779

Novel EGFP reporter cell and mouse models for sensitive imaging and quantification of exon skipping

Hara Y, Mizobe Y, Inoue Y, Hashimoto Y, Motohashi N, Masaki Y, Seio K, Takeda S, Nagata T, Wood M, Inoue T, Aoki Y.

Scientific Reports 2020 Jun 22;10. doi: 10.1038/s41598-020-67077-4

Transcription of DNA duplex containing deoxypseudouridine and deoxypseudoisocytidine, and inhibition of transcription by triplex forming oligonucleotide that recognizes the modified duplex

Seio K, Yamaguchi K, Yamazaki A, Kanamori T, Masaki Y.

Nucleosides, Nucleotides & Nucleic Acids 2020 Mar 4;39(6):892-904. doi: 10.1080/15257770.2020.1714652

Synthesis of Deoxypseudouridine 5′-Triphosphate Bearing the Photoremovable Protecting Group at the N1 Position Capable of Enzymatic Incorporation to DNA

Takeshita L, Yamada Y, Masaki Y, Seio K.

J. Org. Chem. 2020 Jan 7;85:1861-1870. doi: 10.1021/acs.joc.9b02194

Modification of oligonucleotides with weak basic residues via the 2′-O-carbamoylethyl linker for improving nuclease resistance without loss of duplex stability and antisense activity

Masaki Y, Yamamoto K, Yoshida K, Maruyama A, Tomori T, Iriyama Y, Nakajima H, Kanaki T, Seio K.

Org. Biomol Chem. 2019 Apr 29;17:4835-4842. doi: 10.1039/c9ob00668k

31P NMR Study on the Reactions of Amino Acids and Sugar Derivatives with Pyrophosphorous Acid as a Possible Prebiotic Phosphonylating Agent

Seio K, Shiozawa T, Sugiyama D, Ohno K, Tomori T, Masaki Y.

Bull. Chem. Soc. Jpn. 2019 Apr 10;92(4):905-911. doi: 10.1246/bcsj.20180392

DNA triplex-based fluorescence turn-on sensors for adenosine using a fluorescent molecular rotor 5-(3-methylbenzofuran-2-yl) deoxyuridine

Kanamori T, Masaki Y, Oda Y, Ohzeki H, Ohkubo A, Sekine M, Seio K.

Org. Biomol Chem. 2019 Jan 25;17:2077-2080. doi: 10.1039/C8OB02747A

Synthesis of 2′-O-(N-methylcarbamoylethyl) 5-methyl-2-thiouridine and its application to splice-switching oligonucleotides.

Masaki Y, Yamamoto K, Inde T, Yoshida K, Maruyama A, Nagata T, Tanihata J, Takeda S, Sekine M, Seio K.

Bioorg Med Chem Lett. 2019 Jan 15;29(2):160-163. doi: 10.1016/j.bmcl.2018.12.005

Tolerance of N2-heteroaryl modifications on guanine bases in a DNA G-quadruplex

Masaki Y, Inde T, Maruyama A, Seio K.

Org. Biomol Chem. 2019 Jan 4;17:859-866. doi: 10.1039/C8OB03100B

Synthesis of and triplex formation in oligonucleotides containing 2'-deoxy-6-thioxanthosine.

Inde T, Nishizawa S, Hattori Y, Kanamori T, Yuasa H, Seio K, Sekine M, Ohkubo A.

Bioorg Med Chem. 2018 Jul 30;26(13):3785-3790. doi: 10.1016/j.bmc.2018.06.004

Application of 2'-O-(2-N-Methylcarbamoylethyl) Nucleotides in RNase H-Dependent Antisense Oligonucleotides.

Masaki Y, Iriyama Y, Nakajima H, Kuroda Y, Kanaki T, Furukawa S, Sekine M, Seio K.

Nucleic Acid Ther. 2018 Jul 18;28(5):307-311. doi: 10.1089/nat.2018.0738

Deoxynucleoside Triphosphate Containing Pyridazin-3-one Aglycon as a Thymidine Triphosphate Substitute for Primer Extension and Chain Elongation by Klenow fragments.

Tomori T, Nagaoka K, Takeshita L, Shiozawa T, Miyatake Y, Masaki Y, Sekine M, Seio K.

J Org Chem. 2018 Jun 28;83(15):8353-8363. doi: 10.1021/acs.joc.8b00918

Solvent- and environment-dependent fluorescence of modified nucleobases.

Seio K, Kanamori T, Masaki Y.

Tetrahedron Lett. 2018 May 23;59(21):1977-1985. doi: 10.1016/j.tetlet.2018.04.003

Synthesis of photocaged 6-O-(2-nitrobenzyl)guanosine and 4-O-(2-nitrobenzyl) uridine triphosphates for photocontrol of the RNA transcription reaction.

Ohno K, Sugiyama D, Takeshita L, Kanamori T, Masaki Y, Sekine M, Seio K.

Bioorg Med Chem. 2017 Sep 21;25(21):6007-6015. doi: 10.1016/j.bmc.2017.09.032.

Synthesis of oligonucleotides containing 2-N-heteroarylguanine residues and their effect on duplex/triplex stability.

Inde T, Masaki Y, Maruyama A, Ito Y, Makio N, Miyatake Y, Tomori T, Sekine M, Seio K.

Org Biomol Chem. 2017 Oct 11;15(39):8371-8383. doi: 10.1039/c7ob01875d.

A Systematic Study of the Synthesis of 2ʹ-Deoxynucleosides by Mitsunobu Reaction.

Seio K, Tokugawa M, Kaneko K, Shiozawa T, Masaki, Y.

Synlett 2017; 28(15): 2014-2017. doi: 10.1055/s-0036-1588445.

Deformability Calculation for Estimation of the Relative Stability of Chemically Modified RNA Duplexes.

Masaki Y, Sekine M, Seio K.

Curr Protoc Nucleic Acid Chem. 2017 Mar 2;68:7.27.1-7.27.10. doi:10.1002/cpnc.25.

Fluorescence enhancement of oligodeoxynucleotides modified with green fluorescent protein chromophore mimics upon triplex formation.

Kanamori T, Takamura A, Tago N, Masaki Y, Ohkubo A, Sekine M, Seio K.

Org Biomol Chem. 2017 Feb 1;15(5):1190-1197. doi:10.1039/c6ob01278g.