Department of Chemistry and Biomolecular Science
Faculty of Engineering             Ando Lab    

List of Publications

Go to Prof. Ando's list of publications

Go to Prof. Sai's list of publications

Natsuhisa Oka

  1. "Serendipitous one-step synthesis of cyclopentene derivatives from 5'-deoxy-5'-heteroarylsulfonylnucleosides as nucleoside-derived Julia-Kocienski reagents" Oka, N.; Kanda, M.; Furuzawa, M.; Arai, W.; Ando, K. J. Org. Chem. 2021, 86, 16684-16698.

  2. "Synthesis of xanthosine 2-phosphate diesters via phosphitylation of the carbonyl group" Oka, N.; Hirabayashi, H.; Kumada, K.; Ando, K. Bioorg. Med. Chem. Lett. 2021, 54, 128439.

  3. "Stereoselective synthesis of 1,2-cis-glycosyl sulfones and their application in one-pot Julia olefination for the synthesis of exo-glycals" Oka, N.; Suzuki, K.; Mori, A.; Ando, K. Eur. J. Org. Chem. 2021, 5922-5933.

  4. "Stereoselective synthesis of ribofuranoid exo-glycals by one-pot Julia olefination using ribofuranosyl sulfones" Oka, N.; Mori, A.; Suzuki, K.; Ando, K. J. Org. Chem. 2021, 86, 657-673.

  5. "Regioselective O6-diphenylcarbamoylation of 7-deazaguanine derivatives via a stable intermediate 1-(diphenylcarbamoyl)-4-(dimethylamino)pyridinium chloride" Oka, N.; Nakano, K.; Fukuta, A.; Ando, K. Tetrahedron Lett. 2020, 61, 152085.

  6. "Identification of a radical SAM enzyme involved in the synthesis of archaeosine" Yokogawa, T.; Nomura, Y.; Yasuda, A.; Ogino, H.; Hiura, K.; Nakada, S.; Oka, N.; Ando, K.; Kawamura, T.; Hirata, A.; Hori, H.; Ohno, S. Nat. Chem. Biol. 2019, 15, 1148–1155.

  7. "Hydrosilylation of aldehydes catalyzed by diethyl 2-pyridylphosphonate" Oka, N.; Ito, K.; Ando, K. Malaysian J. Anal. Sci. 2019, 23, 648–653.

  8. Oka, N.; Mori, A.; Ando, K. "Stereoselective synthesis of 1-thio-α-D-ribofuranosides using ribofuranosyl iodides as glycosyl donors" Eur. J. Org. Chem. 2018, 6355–6362.

  9. Oka, N.; Fukuta, A.; Ando, K. "A practical synthesis of archaeosine and its base" Tetrahedron 2018, 74, 5709–5714.

  10. Oka, N.; Ori, K.; Ando, K. Synthesis of 2-pyridylthiophosphinic acids and 2-pyridylthiophosphonate monoesters via nucleophilic aromatic substitution. Phosphorus, Sulfur Silicon Relat. Elem. 2017, 192, 454–463.

  11. Nukaga, Y.; Oka, N.; Wada, T. Stereocontrolled solid-phase synthesis of PO/PS chimeric oligodeoxyribonucleotides on an automated synthesizer using an oxazaphospholidine–phosphoramidite method. J. Org. Chem. 2016, 81, 2753–2762.

  12. Oka, N.; Wada, T. Stereocontrolled synthesis of phosphate-modified oligonucleotides. J. Synth. Org. Chem. Jpn.  2016, 74, 31–44.

  13. Nukaga, Y.; Takemura, T.; Iwamoto, N.; Oka, N.; Wada, T. Enhancement of affinity of 2'-O-Me-oligonucleotides for complementary RNA by incorporating a stereoregulated boranophosphate backbone. RSC Adv. 2015, 5, 2392–2395.

  14. Oka, N.; Kajino, R.; Takeuchi, K.; Nagakawa, H.; Ando, K. α-Selective ribofuranosylation of alcohols with ribofuranosyl iodides and triphenylphosphine oxide. J. Org. Chem. 2014, 79, 7656–7664.

  15. Uehara, S.; Hiura, S.; Higashida, R.; Oka, N.; Wada, T. Solid-phase synthesis of P-boronated oligonucleotides by the H-boranophosphonate method. J. Org. Chem. 2014, 79, 3465–3472.

  16. Synthesis of inosine 6-phosphate diesters via phosphitylation of carbonyl oxygen. Oka, N.; Morita, Y.; Itakura, Y.; Ando, K. Chem. Commun. 2013, 49, 11503–11505.

  17. Tatsumi, S.; Matsumura, F.; Oka, N.; Wada, T. Glycosylation of alcohols using glycosyl boranophosphates as glycosyl donors. Tetrahedron Lett. 2013, 54, 3731–3734.

  18. Oka, N.; Murakami, R.; Kondo, T.; Wada, T. Stereocontrolled synthesis of dinucleoside phosphorothioates using a fluorous tag. J. Fluorine Chem. 2013, 150, 85–91.

  19. Nomura, Y.; Onda, Y.; Ohno, S.; Taniguchi, H.; Ando, K.; Oka, N.; Nishikawa, K.; Yokogawa, T. Purification and comparison of native and recombinant tRNA-guanine transglycosylases from Methanosarcina acetivorans. Protein Expr. Purif. 2013, 88, 13–19.

  20. Oka, N.; Ito, K.; Tomita, F.; Ando, K. Synthesis of 2-pyridylphosphinate and thiophosphinate derivatives by nucleophilic aromatic substitution of N-methoxypyridinium tosylates. Chem. Lett. 2012, 41, 1630–1632.

  21. Oka, N.; Sato, K.; Wada, T. Recent progress in the synthesis of glycosyl phosphate derivatives. Trends Glycosci. Glycotechnol. 2012, 24, 152–168.

  22. Nukaga, Y.; Yamada, K.; Ogata, T.; Oka, N.; Wada, T. Stereocontrolled solid-phase synthesis of phosphorothioate oligoribonucleotides using 2'-O-(2-cyanoethoxymethyl)nucleoside 3'-O-oxazaphospholidine monomers. J. Org. Chem. 2012, 77, 7913–7922.

  23. Iwamoto, N.; Oka, N.; Wada, T. Stereocontrolled synthesis of oligodeoxyribonucleoside boranophosphates by an oxazaphospholidine approach using acid-labile N-protecting groups. Tetrahedron Lett. 2012, 53, 4361–4364.

  24. Oka, N.; Takayama, Y.; Ando, K.; Wada, T. Synthesis of nucleoside 5'-boranophosphorothioate derivatives using an H-boranophosphonate monoester as a precursor. Bioorg. Med. Chem. Lett. 2012, 22, 4571–4574.

  25. Oka, N.; Wada, T. Stereocontrolled synthesis of oligonucleotide analogs containing chiral internucleotidic phosphorus atoms. Chem. Soc. Rev. 2011, 40, 5829–5843.

  26. Uchiyama, N.; Ogata, T.; Oka, N.; Wada, T. Trimethylsilyl trifluoromethanesulfonate-promoted reductive 2′-O-arylmethylation of ribonucleoside derivatives. Nucleosides Nucleotides Nucleic Acids 2011, 30, 446–456.

  27. Fujita, S.; Oka, N.; Matsumura, F.; Wada, T. Synthesis of oligo(a-D-glycosyl phosphate) derivatives by a phosphoramidite method via boranophosphate intermediates. J. Org. Chem. 2011, 76, 2468–2659.

  28. Nagata, S.; Hamasaki, T.; Uetake, K.; Masuda, H.; Takagaki, K.; Oka, N.; Wada, T.; Ohgi, T.; Yano, J. Synthesis and biological activity of artificial mRNA prepared with novel phosphorylating reagents. Nucleic Acids Res. 2010, 38, 7845–7857.

  29. Matsumura, F.; Tatsumi, S.; Oka, N.; Wada, T. Rapid glycosylations under extremely mild acidic conditions. Use of ammonium salts to activate glycosyl phosphites via P-protonation. Carbohydr. Res. 2010, 345, 1211–1215.

  30. Sato, K.; Oka, N.; Fujita, S.; Matsumura, F.; Wada, T. 1,2-Trans-Selective Synthesis of Glycosyl Boranophosphates and Their Utility as Building Blocks for the Synthesis of Phosphodiester-Linked Disaccharides. J. Org. Chem. 2010, 75, 2147–2156.

  31. Oka, N.; Maizuru, Y.; Shimizu, M.; Wada, T. Solid-phase synthesis of oligodeoxyribonucleotides without base protection utilizing O-selective reaction of oxazaphospholidine derivatives. Nucleosides Nucleotides Nucleic Acids 2010, 29, 144–154.

  32. Oka, N.; Nakamura, M.; Soeda, N.; Wada, T. Stereocontrolled synthesis of tertiary silanes via optically pure 1,3,2-oxazasilolidine derivatives. J. Organomet. Chem. 2009, 694, 2171–2178.

  33. Higashida, R.; Oka, N.; Kawanaka, T.; Wada, T. Nucleoside H-boranophosphonates: a new class of boron-containing nucleotide analogues. Chem. Commun. 2009, 2466–2468.

  34. Oka, N.; Kondo, T.; Fujiwara, S.; Maizuru, Y.; Wada, T. Stereocontrolled synthesis of oligoribonucleoside phosphorothioates by an oxazaphospholidine approach. Org. Lett. 2009, 11, 967–970.

  35. Iwamoto, N.; Oka, N.; Sato, T.; Wada, T. Stereocontrolled solid-phase synthesis of oligonucleoside H-phosphonates by an oxazaphospholidine approach. Angew. Chem. Int. Ed. 2009, 48, 496–499.

  36. Oka, N.; Yamamoto, M.; Sato, T.; Wada, T. Solid-phase synthesis of stereoregular oligodeoxyribonucleoside phosphorothioates using bicyclic oxazaphospholidine derivatives as monomer units. J. Am. Chem. Soc. 2008, 130, 16031–16037.

  37. Matsumura, F.; Oka, N.; Wada, T. Stereoselective synthesis of a-glycosyl phosphites and phosphoramidites via O-selective glycosylation of H-phosphonate derivatives. Org. Lett. 2008, 10, 5297–5300.

  38. Enya, Y.; Nagata, S.; Masutomi, Y.; Kitagawa, H.; Takagaki, K.; Oka, N.; Wada, T.; Ohgi, T.; Yano, J. Chemical synthesis of diastereomeric diadenosine boranophosphate (ApbA) from 2'-O-(2-cyanoethoxymethyl)adenosine by the boranophosphotriester method. Bioorg. Med. Chem. 2008, 20, 9154–9160.

  39. Matsumura, F.; Oka, N.; Wada, T. Synthesis of glycosyl boranophosphates and their applications as precursors of glycosyl phosphate analogues. Org. Lett. 2008, 10, 1557–1560.

  40. Watanabe, K.; Toh, Y.; Suto, K.; Shimizu, Y.; Oka, N.; Wada, T.; Tomita, K. Protein-based peptide-bond formation by aminoacyl-tRNA protein transferase. Nature 2007, 449, 867–871.

  41. Imoto, S.; Patro, J. N.; Jiang, Y. L.; Oka, N.; Greenberg, M. M. Synthesis, DNA polymerase incorporation, and enzymatic phosphate hydrolysis of formamidopyrimidine nucleoside triphosphates. J. Am. Chem. Soc. 2006, 128, 14606–14611.

  42. Wada, T.; Maizuru, Y.; Shimizu, M.; Oka, N.; Saigo, K. Stereoselective synthesis of dinucleoside boranophosphates by an oxazaphospholidine method. Bioorg. Med. Chem. Lett. 2006, 16, 3111–3114.

  43. Oka, N.; Shimizu, M.; Saigo, K.; Wada, T. 1,3-Dimethyl-2-(3-nitro-1,2,4-triazol-1-yl)-2-pyrrolidin-1-yl-1,3,2-diazaphospholidinium hexafluorophosphate: a powerful condensing reagent for phosphate and phosphonate esters. Tetrahedron 2006, 62, 3667–3673.

  44. Kato, Y.; Oka, N.; Wada, T. Highly chemo- and regioselective phosphitylation of unprotected 2'-deoxyribonucleosides. Tetrahedron Lett. 2006, 47, 2501–2505.

  45. Oka, N.; Greenberg, M. M. The effect of the 2-amino group of 7,8-dihydro-8-oxo-2'-deoxyguanosine on translesion synthesis and duplex stability. Nucleic Acids Res. 2005, 33, 1637–1643.

  46. Shimizu, M.; Wada, T.; Oka, N.; Saigo, K. A novel method for the synthesis of dinucleoside boranophosphates by a borano-phospho-triester method. J. Org. Chem. 2004, 69, 5261–5268.

  47. Oka, N.; Sanghvi, Y. S.; Theodorakis, E. A. 3,3'-Oxybis(dimethoxytrityl chloride) (O-DMTCl): synthesis and applications of a novel bifunctional protecting group. Bioorg. Med. Chem. Lett. 2004, 14, 3241–3244.

  48. Oka, N.; Sanghvi, Y. S.; Theodorakis, E. A. 1,2-Ethylene-3,3-bis(4',4''-dimethoxytrityl chloride) (E-DMT): synthesis and applications of a novel protecting reagent. Synlett 2004, 5, 823–826.

  49. Oka, N.; Wada, T.; Saigo, K. An oxazaphospholidine approach for the stereocontrolled synthesis of oligonucleoside phosphorothioates. J. Am. Chem. Soc. 2003, 125, 8307–8317.

  50. Oka, N.; Wada, T.; Saigo, K. Diastereo-controlled synthesis of dinucleoside phosphorothioates using a novel class of activators, dialkyl(cyanomethyl)ammonium tetrafluoroborates. J. Am. Chem. Soc. 2002, 124, 4962–4963.

  51. Wada, T.; Shimizu, M.; Oka, N.; Saigo, K. A new boranophosphorylation reaction for the synthesis of deoxyribonucleoside boranophosphates. Tetrahedron Lett. 2002, 43, 4137–4140.

  52. Matsui, S.; Oka, N.; Hashimoto, Y.; Saigo, K. Application of cis-2-amino-3,3-dimethyl-1-indanol as an efficient chiral auxiliary to the asymmetric Ireland-Claisen rearrangement. Improvement of the diastereoselectivity by combinational use of chlorodimethylsilane as a silylating agent. Enantiomer 2000, 5, 105–108.

Books

  1. 岡 夏央，松村 史子，和田 猛  複合糖質の化学と最新応用技術 第3章 糖-1-リン酸誘導体の化学合成（2009, シーエムシー出版）