工学部 化学・生命工学科 安藤研究室  

   

研究業績

Go to Prof. Ando's list of publications

Go to Prof. Sai's list of publications

岡 夏央

  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, 11481155.

  7. "Hydrosilylation of aldehydes catalyzed by diethyl 2-pyridylphosphonate" Oka, N.; Ito, K.; Ando, K. Malaysian J. Anal. Sci. 2019, 23, 648653.

  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, 63556362.

  9. Oka, N.; Fukuta, A.; Ando, K. "A practical synthesis of archaeosine and its base" Tetrahedron 2018, 74, 57095714.

  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, 454463.

  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, 27532762.

  12. 夏央・和田 猛 リン原子修飾オリゴ核酸の立体選択的合成 有機合成化学協会誌   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, 23922395.

  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, 76567664.

  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, 34653472.

  16. Oka, N.; Morita, Y.; Itakura, Y.; Ando, K. Synthesis of inosine 6-phosphate diesters via phosphitylation of carbonyl oxygen. Chem. Commun. 2013, 49, 1150311505.

  17. Tatsumi, S.; Matsumura, F.; Oka, N.; Wada, T. Glycosylation of alcohols using glycosyl boranophosphates as glycosyl donors. Tetrahedron Lett. 2013, 54, 37313734.

  18. Oka, N.; Murakami, R.; Kondo, T.; Wada, T. Stereocontrolled synthesis of dinucleoside phosphorothioates using a fluorous tag. J. Fluorine Chem. 2013, 150, 8591.

  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, 1319.

  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, 16301632.

  21. Oka, N.; Sato, K.; Wada, T. Recent progress in the synthesis of glycosyl phosphate derivatives. Trends Glycosci. Glycotechnol. 2012, 24, 152168.

  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, 79137922.

  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, 43614364.

  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, 45714574.

  25. Oka, N.; Wada, T. Stereocontrolled synthesis of oligonucleotide analogs containing chiral internucleotidic phosphorus atoms. Chem. Soc. Rev. 2011, 40, 58295843.

  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, 446456.

  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, 24682659.

  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, 78457857.

  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, 12111215.

  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, 21472156.

  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, 144154.

  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, 1460614611.

  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, 31113114.

  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, 52615268.

  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, 32413244.

  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, 823826.

  49. Oka, N.; Wada, T.; Saigo, K. An oxazaphospholidine approach for the stereocontrolled synthesis of oligonucleoside phosphorothioates. J. Am. Chem. Soc. 2003, 125, 83078317.

  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, 49624963.

  51. Wada, T.; Shimizu, M.; Oka, N.; Saigo, K. A new boranophosphorylation reaction for the synthesis of deoxyribonucleoside boranophosphates. Tetrahedron Lett. 2002, 43, 41374140.

  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, 105108.

著書等

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