Nucleic Acids Chemistry
KOHJI SEIO's group
Tokyo Institute of Technology
Department of Life Science and Technology

Publications


| 2022 | 2021 | 2020 | 2019 | 2018 | 2017 | 2016 | 2015 | 2014 | 2013 | 2012 | 2011 | 2010 | 2009 | 2008 | 2007 |
| Publication (1995-2006) |

2022

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.org/10.1039/D2OB01667B.


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



2021

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



2020

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



2019

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



A theoretical study on the elimination reaction of acrylonitrile from 2′-O-cyanoethylated nucleosides by Bu4NF.
Ando K, Saneyoshi H, Seio K, Sekine M.
Tetrahedron 2019 Jan 3;75(1):1-9. doi: 10.1016/j.tet.2018.11.042



2018

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




2017

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.

2016

Enzymatic synthesis and reverse transcription of RNAs incorporating 2′-O-carbamoyl uridine triphosphate
Masaki Y, Ito H, Oda Y, Yamazaki K, Tago N, Ohno K, Ishii N, Tsunoda H, Kanamori T, Ohkubo A, Sekine M, Seio K.
Chem Commun (Camb). 2016 Oct 25;52(87):12889-12892. doi:10.1039/C6CC05796A

Photo-controlled binding of MutS to photo-caged DNA duplexes incorporating 4-O-(2-nitrobenzyl) or 4-O-[2-(2-nitrophenyl)propyl]thymidine
Seio K, Ohno Y, Ohno K, Takeshita L, Kanamori T, Masaki Y, Sekine M.
Bioorg Med Chem Lett. 2016 Oct 1;26(19):4861-3. doi: 10.1016/j.bmcl.2016.07.075.

An Effective Strategy for a Conformer-Selective Detection of Short-Lived Excited State Species: Application to the IR Spectroscopy of the N1H Keto Tautomer of Guanine
Asami H, Tokugawa M, Masaki Y, Ishiuchi S, Gloaguen E, Seio K, Saigusa H, Fujii M, Sekine M, Mons M.
J Phys Chem A. 2016 Apr 14;120(14):2179-84. doi: 10.1021/acs.jpca.6b01194.

7-(Benzofuran-2-yl)-7-deazadeoxyguanosine as a fluorescence turn-ON probe for single-strand DNA binding protein
Tokugawa M, Masaki Y, Canggadibrata J C, Kaneko K, Shiozawa T, Kanamori T, Grøtli M, Wilhelmsson L M, Sekine M, Seio K.
Chem Commun (Camb). 2016 Mar 7;52(19):3809-12. doi: 10.1039/c5cc09700b.


Synthesis of 5-[3-(2-aminopyrimidin-4-yl)aminopropyn-1-yl]uracil derivative that recognizes Ade-Thy base pairs in double-stranded DNA
Ito Y, Masaki Y, Kanamori T, Ohkubo A, Seio K, Sekine M.
Bioorg Med Chem Lett. 2016 Jan 1;26(1):194-6. doi: 10.1016/j.bmcl.2015.11.003.

2015

A New Microfluidic Phase-Transfer Reaction Using HPLC Guard Columns as the Reactor for the N3-Protection of Uridine Derivatives
Tago N, Masaki Y, Nagasawa H, Kanamori T, Ohkubo A, Seio K, Sekine M.
Synlett. 2015 26(18): 2578-2582. doi:10.1055/s-0035-1560264

Design, Synthesis, and Properties of Phosphoramidate 2′,5′-Linked Branched RNA: Toward the Rational Design of Inhibitors of the RNA Lariat Debranching Enzyme
Tago N, Katolik A, Clark N E, Montemayor E J, Seio K, Sekine M. Hart P J, Damha M J.
J Org Chem. 2015 Oct 16;80(20):10108-18. doi: 10.1021/acs.joc.5b01719.

Synthesis and triplex-forming properties of oligonucleotides capable of recognizing corresponding DNA duplexes containing four base pairs
Ohkubo A, Yamada K, Ito Y, Yoshimura K, Miyauchi K, Kanamori T, Masaki Y, Seio K, Yuasa H, Sekine M.
Nucleic Acids Res., 2015 May 3;43.5675-5686. doi:10.1093/nar/gkv496

Synthesis of Peptide Nucleic Acids Containing Pyridazine Derivatives As Cytosine and Thymine Analogs, and Their Duplexes with Complementary Oligodeoxynucleotides
Tomori T, Miyatake Y, Sato Y, Kanamori T, Masaki Y, Ohkubo A, Sekine M, Seio K.
Org. Lett., 2015 Mar 10;17:1609–1612. doi:10.1021/acs.orglett.5b00522

Enhancement of exon skipping in mdx52 mice by 2´-O-methyl-2-thioribothymidine incorporation into phosphorothioate oligonucleotides
Masaki Y, Inde T, Nagata T, Tanihata J, Kanamori T, Seio K, Takeda S, Sekine M.
Med. Chem. Commun., 2015 Apr 1;6:630-633. doi:10.1039/C4MD00468J


Synthesis of Responsive Fluorescent Nucleobases 7-(Benzofuran-2-yl)-7-deazahypoxanthine and 7-(Benzofuran-2-yl)-7-deazaguanine using Cross-coupling Reaction
Tokugawa M, Kaneko K, Saito M, Kanamori T, Masaki Y, Ohkubo A, Sekine M, Seio K.
Chem Lett. 2015 Jan 5;44:64-66. doi:10.1246/cl.140879

Controlling the Fluorescence of Benzofuran-Modified Uracil Residues in Oligonucleotides by Triple-Helix Formation
Kanamori T, Ohzeki H, Masaki Y, Ohkubo A, Takahashi M, Tsuda K, Ito T, Shirouzu M, Kuwasako K, Muto Y, Sekine M, Seio K.
ChemBioChem. 2015 Jan 2;16:167-176. doi:10.1002/cbic.201402346

2014

Synthesis and properties of oligonucleotides modified with 2´-O-(2-carboxyethyl)nucleotides and their carbamoyl derivatives
Yamada T, Masaki Y, Okaniwa N, Kanamori T, Ohkubo A, Tsunoda H, Seio K, Sekine M.
Org Biomol Chem. 2014 Jun 27;12(33):6457-6464. doi:10.1039/C4OB01260G

A new modified cytosine base capable of base pairing with guanine using four hydrogen bonds
Yamada K, Masaki Y, Tsunoda H, Ohkubo A, Seio K, Sekine M.
Org Biomol Chem. 2014 Feb 11;12(14):2255-2262. doi:10.1039/C3OB42420K

Properties of 5- and/or 2-modified 2′-O-cyanoethyl uridine residue: 2′-O-cyanoethyl-5-propynyl-2-thiouridine as an efficient duplex stabilizing component.
Masaki Y, Miyasaka R, Hirai K, Kanamori T, Tsunoda H, Ohkubo A, Seio K, Sekine M.
Org Biomol Chem. 2014 Feb 21;12(7):1157-1162. doi:10.1039/C3OB41983E

2013

Assembly of pyrene-modified DNA/RNA duplexes incorporating a G-rich single strand region
Seio K, Tokugawa M, Tsunoda H, Ohkubo A, Arisaka H, Sekine M.
Bioorg Med Chem Lett. 2013 Dec 15;23(24):6822-6824. doi: 10.1016/j.bmcl.2013.10.012.

Modified oligodeoxynucleotide primers for reverse-transcription of target RNAs that can discriminate among length variants at the 3′-terminus.
Iijima Y, Kojima S, Kodama E, Kurohagi S, Kanamori T, Masaki Y, Ohkubo A, Sekine M, Seio K.
Org Biomol Chem. 2013 Oct 2;11(47):8276-8282 doi:10.1039/C3OB41901K

Chemical synthesis of U1 snRNA derivatives.
Ohkubo A, Kondo Y, Suzuki M, Kobayashi H, Kanamori T, Masaki Y, Seio K, Nagai K, Sekine M.
Org Lett. 2013 August 16;15(17):4386-4389. doi:10.1021/ol401917r

Fluorescent properties of oligonucleotides doubly modified with an indole-fused cytosine analog and 2-aminopurine.
Seio K, Kanamori T, Tokugawa M, Ohzeki H, Masaki Y, Tsunoda H, Ohkubo A, Sekine M.
Bioorg Med Chem. 2013 June 1;21(11):3197-3201. doi: 10.1016/j.bmc.2013.03.034.

Base recognition of gap sites in DNA–DNA and DNA–RNA duplexes by short oligonucleotides.
Yamada K, Ohkubo A, Esaka Y, Kanamori T, Masaki Y, Seio K, Sekine M.
Bioorg Med Chem Lett. 2013 June 1;23(11):3448-3451. doi: 10.1016/j.bmcl.2013.03.054.

Remarkable stabilization of antiparallel DNA triplexes by strong stacking effects of consecutively modified nucleobases containing thiocarbonyl groups.
Yamada K, Hattori Y, Inde T, Kanamori T, Ohkubo A, Seio K, Sekine M.
Bioorg Med Chem Lett. 2013 Feb 1;23(3):776-778. pii: S0960-894X(12)01531-4. doi: 10.1016/j.bmcl.2012.11.079.

2012

Prediction of the stability of modified RNA duplexes based on deformability analysis: oligoribonucleotide derivatives modified with 2'-O-cyanoethyl-5-propynyl-2-thiouridine as a promising component.
Masaki Y, Miyasaka R, Hirai K, Tsunoda H, Ohkubo A, Seio K, Sekine M.
Chem Commun (Camb). 2012 Jul 25;48(58):7313-5. doi: 10.1039/c2cc33409g.

Synthesis and properties of cationic 2'-O-[N-(4-aminobutyl)carbamoyl] modified oligonucleotides.
Seio K, Tokugawa M, Kanamori T, Tsunoda H, Ohkubo A, Sekine M.
Bioorg Med Chem Lett. 2012 Apr 1;22(7):2470-3. doi: 10.1016/j.bmcl.2012.02.012.

Formation of new base pairs between inosine and 5-methyl-2-thiocytidine derivatives.
Ohkubo A, Nishino Y, Ito Y, Tsunoda H, Seio K, Sekine M.
Org Biomol Chem. 2012 Mar 14;10(10):2008-10. doi: 10.1039/c2ob06641f.

Development of an efficient method for phosphorodiamidate bond formation by using inorganic salts.
Harakawa T, Tsunoda H, Ohkubo A, Seio K, Sekine M.
Bioorg Med Chem Lett. 2012 Feb 1;22(3):1445-7. doi: 10.1016/j.bmcl.2011.12.021.

Synthesis of 5'-terminal capped oligonucleotides using O-N phosphoryl migration of phosphoramidite derivatives.
Ohkubo A, Tago N, Yokouchi A, Nishino Y, Yamada K, Tsunoda H, Seio K, Sekine M.
Org Lett. 2012 Jan 6;14(1):10-3. doi: 10.1021/ol2026075.

DNA duplexes and triplex-forming oligodeoxynucleotides incorporating modified nucleosides forming stable and selective triplexes.
Kanamori T, Masaki Y, Mizuta M, Tsunoda H, Ohkubo A, Sekine M, Seio K.
Org Biomol Chem. 2012 Feb 7;10(5):1007-13. doi: 10.1039/c1ob06411h.

Short-RNA selective binding of oligonucleotides modified using adenosine and guanosine derivatives that possess cyclohexyl phosphates as substituents.
Seio K, Kurohagi S, Kodama E, Masaki Y, Tsunoda H, Ohkubo A, Sekine M.
Org Biomol Chem. 2012 Feb 7;10(5):994-1006. doi: 10.1039/c1ob06580g.

2011

Stable triplex formation using the strong stacking effect of consecutive thionucleoside moieties.
Ohkubo A, Nishino Y, Yokouchi A, Ito Y, Noma Y, Kakishima Y, Masaki Y, Tsunoda H, Seio K, Sekine M.
Chem Commun (Camb). 2011 Dec 14;47(46):12556-8. doi: 10.1039/c1cc14339e.

Synthesis of 2'-O-[2-(N-methylcarbamoyl)ethyl]ribonucleosides using oxa-Michael reaction and chemical and biological properties of oligonucleotide derivatives incorporating these modified ribonucleosides.
Yamada T, Okaniwa N, Saneyoshi H, Ohkubo A, Seio K, Nagata T, Aoki Y, Takeda S, Sekine M.
J Org Chem. 2011 May 6;76(9):3042-53. doi: 10.1021/jo101963z.

Biochemical behavior of N-oxidized cytosine and adenine bases in DNA polymerase-mediated primer extension reactions.
Tsunoda H, Kudo T, Masaki Y, Ohkubo A, Seio K, Sekine M.
Nucleic Acids Res. 2011 Apr;39(7):2995-3004. doi: 10.1093/nar/gkq914.

Versatile Site-Specific Conjugation of Small Molecules to siRNA Using Click Chemistry.
Yamada T, Peng C G, Matsuda S, Addepalli H, Jayaprakash K N, Alam Md R, Mills K, Maier M A, Charisse K, Sekine M, Manoharan M, Rajeev K G.
J Org Chem. 2011 Feb 7;76(5):1198-1211. doi: 10.1021/jo101761g.

Synthesis and hybridization properties of 2'-O-methylated oligoribonucleotides incorporating 2'-O-naphthyluridines.
Sekine M, Oeda Y, Iijima Y, Taguchi H, Ohkubo A, Seio K.
Org Biomol Chem. 2011 Jan 7;9(1):210-8. doi: 10.1039/c0ob00248h.

Synthesis and triplex-forming properties of oligonucleotides containing thio-substituted C-nucleoside 4-thiopseudoisocytidine.
Cao, SQ; Okamoto, I; Tsunoda, H; Ohkubo, A; Seio, K; Sekine, M
Tetrahedron Lett. 2011, 52(3), 407-410 doi: 10.1016/j.tetlet.2010.11.065

2010
Synthesis of oligodeoxynucleotides using fully protected deoxynucleoside 3'-phosphoramidite building blocks and base recognition of oligodeoxynucleotides incorporating N3-cyano-ethylthymine.
Tsunoda H, Kudo T, Ohkubo A, Seio K, Sekine M.
Molecules. 2010 Oct 27;15(11):7509-31. doi: 10.3390/molecules15117509.

Oligonucleotide synthesis involving deprotection of amidine-type protecting groups for nucleobases under acidic conditions.
Ohkubo A, Kuwayama Y, Nishino Y, Tsunoda H, Seio K, Sekine M.
Org Lett. 2010 Jun 4;12(11):2496-9. doi: 10.1021/ol100676j.

Linear relationship between deformability and thermal stability of 2'-O-modified RNA hetero duplexes.
Masaki Y, Miyasaka R, Ohkubo A, Seio K, Sekine M.
J Phys Chem B. 2010 Feb 25;114(7):2517-24. doi: 10.1021/jp909851j.

Synthesis of 6-N-(benzothiazol-2-yl)deoxyadenosine and its exciton-coupled circular dichroism.
Masaki Y, Ohkubo A, Seio K, Sekine M.
Bioorg Med Chem. 2010 Jan 15;18(2):567-72. doi: 10.1016/j.bmc.2009.12.009.

Synthesis and biochemical properties of oligodeoxynucleotides acylated by the chemically stable 2-(trimethylsilyl)benzoyl (TMSBz) group at the 5 ' or 3 ' terminus.
Yamada, K; Taguchi, H; Ohkubo, A; Seio, K; Sekine, M
Tetrahedron Lett. 2010, 51(39), 5173-5176. doi: 10.1016/j.tetlet.2010.07.121

Synthesis and Hybridization Properties of Oligonucleotides Incorporating Bi- and Tricyclic Cytosine Derivatives.
Ohkubo, A; Sakaue, T; Tsunoda, H; Seio, K; Sekine, M
Chem. Lett. 2010, 39(7), 726-727 doi: 10.1246/cl.2010.726

Synthesis of oligodeoxynucleotides using the oxidatively cleavable 4-methoxytritylthio (MMTrS) group for protection of the 5 '-hydroxyl group.
Seio, K; Shiraishi, M; Utagawa, E; Ohkubo, A; Sekine, M
New J. Chem. 2010, 34(5), 984-992 doi: 10.1039/b9nj00678h

2009


Microwave-assisted synthesis of 2'-O-aryluridine derivatives.
Oeda Y, Iijima Y, Taguchi H, Ohkubo A, Seio K, Sekine M.
Org Lett. 2009 Dec 17;11(24):5582-5. doi: 10.1021/ol902142w.

Synthesis and hybridization of 2'-O-methyl-RNAs incorporating 2'-O-carbamoyluridine and unique participation of the carbamoyl group in U-G base pair.
Seio K, Tawarada R, Sasami T, Serizawa M, Ise M, Ohkubo A, Sekine M.
Bioorg Med Chem. 2009 Oct 15;17(20):7275-80. doi: 10.1016/j.bmc.2009.08.053.

Synthesis and properties of nucleoside derivatives acylated by chemically stable 2-(trimethylsilyl)benzoyl group.
Yamada K, Taguchi H, Ohkubo A, Seio K, Sekine M.
Bioorg Med Chem. 2009 Aug 15;17(16):5928-32. doi: 10.1016/j.bmc.2009.07.003.

Fluorescence properties of pyrimidopyrimidoindole nucleoside dC(PPI) incorporated into oligodeoxynucleotides.
Mizuta M, Seio K, Ohkubo A, Sekine M.
J Phys Chem B. 2009 Jul 16;113(28):9562-9. doi: 10.1021/jp807562c.

Efficient solid-phase synthesis of oligodeoxynucleotides having a 5'-terminal 2,2,7-trimethylguanosine pyrophosphate linkage.
Ohkubo A, Sasaki K, Noma Y, Tsunoda H, Seio K, Sekine M.
Bioorg Med Chem. 2009 Jul 1;17(13):4819-24. doi: 10.1016/j.bmc.2009.04.073.

Synthesis of terminally modified oligonucleotides and their hybridization dependence on the size of the target RNAs.
Seio K, Takaku Y, Miyazaki K, Kurohagi S, Masaki Y, Ohkubo A, Sekine M.
Org Biomol Chem. 2009 Jun 7;7(11):2440-51. doi: 10.1039/b900301k.

Introduction of 3'-terminal nucleosides having a silyl-type linker into polymer supports without base protection.
Ohkubo A, Noma Y, Aoki K, Tsunoda H, Seio K, Sekine M.
J Org Chem. 2009 Apr 3;74(7):2817-23. doi: 10.1021/jo9000965.

New thermolytic carbamoyl groups for the protection of nucleobases.
Ohkubo A, Kasuya R, Miyata K, Tsunoda H, Seio K, Sekine M.
Org Biomol Chem. 2009 Feb 21;7(4):687-94. doi: 10.1039/b816831h.

Synthesis of oligodeoxynucleotides incorporating 2-N-carbamoylguanine and evaluation of the hybridization properties.
Sasami T, Odawara Y, Ohkubo A, Sekine M, Seio K.
Bioorg Med Chem. 2009 Feb 1;17(3):1398-403. doi: 10.1016/j.bmc.2008.11.042.

Synthesis and triplex formation of oligonucleotides containing 8-thioxodeoxyadenosine.
Miyata K, Tamamushi R, Tsunoda H, Ohkubo A, Seio K, Sekine M.
Org Lett. 2009 Feb 5;11(3):605-8. doi: 10.1021/ol802622s.

Mechanistic studies on oxidative condensation of a thymidine 3'-H-phosphonate derivative with 3 '-O-acetylthymidine
Tawarada, R; Seio, K; Sekine, M
Arkivoc 2009, 264-273.

Synthesis of 4-Thiopseudoisocytidine and 4-Thiopseudouridine as Components of Triplex-forming Oligonucleotides
Okamoto, I; Cao, SQ; Tanaka, H; Seio, K; Sekine, M
Chem. Lett. 2009, 38(2), 174-175. doi: 10.1246/cl.2009.174

Computational evaluation of the stability of 2 '-O-methyl-RNA/RNA duplexes incorporating 3-deazaguanine derivatives by ab initio calculations and a molecular dynamics simulation
Sasami, T; Tawarada, R; Ohkubo, A; Sekine, M; Seio, K
Theochem 2009, 54-60. doi: 10.1016/j.theochem.2008.12.012

2008


Hybridization-dependent fluorescence of oligodeoxynucleotides incorporating new pyrene-modified adenosine residues.
Seio K, Mizuta M, Tasaki K, Tamaki K, Ohkubo A, Sekine M.
Bioorg Med Chem. 2008 Sep 1;16(17):8287-93. doi: 10.1016/j.bmc.2008.05.042. Epub 2008 May 22.

New nucleotide pairs for stable DNA triplexes stabilized by stacking interaction.
Mizuta M, Banba J, Kanamori T, Tawarada R, Ohkubo A, Sekine M, Seio K.
J Am Chem Soc. 2008 Jul 30;130(30):9622-3. doi: 10.1021/ja800991m. Epub 2008 Jul 9.

O-selective condensation using P-N bond cleavage in RNA synthesis without base protection.
Ohkubo A, Kuwayama Y, Kudo T, Tsunoda H, Seio K, Sekine M.
Org Lett. 2008 Jul 3;10(13):2793-6. doi: 10.1021/ol800911b. Epub 2008 Jun 6.

Study of the base discrimination ability of DNA and 2'-O-methylated RNA oligomers containing 2-thiouracil bases towards complementary RNA or DNA strands and their application to single base mismatch detection.
Okamoto I, Seio K, Sekine M.
Bioorg Med Chem. 2008 Jun 1;16(11):6034-41. doi: 10.1016/j.bmc.2008.04.053. Epub 2008 Apr 25.

Efficient synthesis of functionalized oligodeoxyribonucleotides with base-labile groups using a new silyl linker.
Ohkubo A, Kasuya R, Aoki K, Kobori A, Taguchi H, Seio K, Sekine M.
Bioorg Med Chem. 2008 May 1;16(9):5345-51. doi: 10.1016/j.bmc.2008.02.076. Epub 2008 Feb 29.

'Protected DNA Probes' capable of strong hybridization without removal of base protecting groups.
Ohkubo A, Kasuya R, Sakamoto K, Miyata K, Taguchi H, Nagasawa H, Tsukahara T, Watanobe T, Maki Y, Seio K, Sekine M.
Nucleic Acids Res. 2008 Apr;36(6):1952-64. doi: 10.1093/nar/gkm927. Epub 2008 Feb 13.

Binding of MutS protein to oligonucleotides containing a methylated or an ethylated guanine residue, and correlation with mutation frequency.
Taira K, Nakamura S, Nakano K, Maehara D, Okamoto K, Arimoto S, Loakes D, Worth L Jr, Schaaper RM, Seio K, Sekine M, Negishi K, Negishi T.
Mutat Res. 2008 Apr 2;640(1-2):107-12. doi: 10.1016/j.mrfmmm.2007.12.009. Epub 2007 Dec 28.

Synthesis and properties of DNA oligomers containing 2'-deoxynucleoside N-oxide derivatives.
Tsunoda H, Ohkubo A, Taguchi H, Seio K, Sekine M.
J Org Chem. 2008 Feb 15;73(4):1217-24. doi: 10.1021/jo7021845. Epub 2008 Jan 18.

Synthesis and properties of oligonucleotides with iodo-substituted aromatic aglycons: investigation of possible halogen bonding base pairs.
Tawarada R, Seio K, Sekine M.
J Org Chem. 2008 Jan 18;73(2):383-90. Epub 2007 Dec 15.

2007


A pyrimidopyrimidoindole nucleoside (dC PPI): photophysical properties and thermal stability of the modified DNA duplexes.
Mizuta M, Seio K, Miyata K, Ohkubo A, Taguchi H, Sekine M.
Nucleosides Nucleotides Nucleic Acids. 2007;26(10-12):1335-8.

Synthesis and properties of oligodeoxynucleotides containing 5-carboxy-2'-deoxycytidines.
Sumino M, Ohkubo A, Taguchi H, Seio K, Sekine M.
Bioorg Med Chem Lett. 2008 Jan 1;18(1):274-7. Epub 2007 Oct 30.

Synthesis of branched oligonucleotides with three different sequences using an oxidatively removable tritylthio group.
Utagawa E, Ohkubo A, Sekine M, Seio K.
J Org Chem. 2007 Oct 26;72(22):8259-66. Epub 2007 Sep 27.

An effective method for the in situ synthesis of DNA-CPG conjugates using chemical ligation technology as tools for SNP analysis.
Ohkubo A, Tanaka K, Taguchi H, Seio K, Nagasawa H, Tsukahara T, Sekine M.
Bioorg Med Chem Lett. 2007 Nov 1;17(21):5969-73. Epub 2007 Aug 21.

Synthesis and hybridization properties of oligodeoxynucleotides incorporating 2-N-carbamoylguanine derivatives as guanine analogs.
Sasami T, Odawara Y, Ohkubo A, Sekine M, Seio K.
Tetrahedron Lett. 2007 Jul 23;48(30):5325-5329. Epub 2007 May 16.

Fluorescent pyrimidopyrimidoindole nucleosides: control of photophysical characterizations by substituent effects.
Mizuta M, Seio K, Miyata K, Sekine M.
J Org Chem. 2007 Jul 6;72(14):5046-55. Epub 2007 Jun 8.

Highly selective recognition of cytosine over uracil and adenine by a guanine analogue, 2-N-acetyl-3-deazaguanine, in 2'-O-methyl-RNA/RNA and DNA duplexes.
Seio K, Sasami T, Ohkubo A, Ando K, Sekine M.
J Am Chem Soc. 2007 Feb 7;129(5):1026-7. No abstract available.

Synthesis and fluorescent properties of bi- and tricyclic 4-N-carbamoyldeoxycytidine derivatives.
Miyata K, Mineo R, Tamamushi R, Mizuta M, Ohkubo A, Taguchi H, Seio K, Santa T, Sekine M.
J Org Chem. 2007 Jan 5;72(1):102-8.


Publication list (pdf) 1995-2006