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Development on new methodology for optical resolution using plant glycosyltransferases and its pharmacological exploitation

Research Project

Project/Area Number 19790018
Research Category

Grant-in-Aid for Young Scientists (B)

Allocation TypeSingle-year Grants
Research Field Chemical pharmacy
Research InstitutionOita University

Principal Investigator

SHIMODA Kei  Oita University, 医学部, 准教授 (40284153)

Project Period (FY) 2007 – 2010
Project Status Completed (Fiscal Year 2010)
Budget Amount *help
¥3,800,000 (Direct Cost: ¥3,200,000、Indirect Cost: ¥600,000)
Fiscal Year 2010: ¥780,000 (Direct Cost: ¥600,000、Indirect Cost: ¥180,000)
Fiscal Year 2009: ¥780,000 (Direct Cost: ¥600,000、Indirect Cost: ¥180,000)
Fiscal Year 2008: ¥1,040,000 (Direct Cost: ¥800,000、Indirect Cost: ¥240,000)
Fiscal Year 2007: ¥1,200,000 (Direct Cost: ¥1,200,000)
Keywords有機合成化学 / バイオテクノロジー / 酵素 / 有機化学 / タンパク質 / 酵素反応
Research Abstract

A plant xylosyltransferase was isolated from cultured plant cells by chromatographies using ion-exchange column, affinity column, and size excluding column. The new enzymatic resolution of (RS)-1-phenylalkyl β-D-glucosides has been achieved by stereoselective xylosylation with the enzyme to give (R)-1-phenylalkyl β-primeverosides and unreacted (S)-1-phenylalkyl β-D-glucosides with high diastereoselectivity.

Report

(6 results)
  • 2010 Annual Research Report   Final Research Report ( PDF )
  • 2009 Annual Research Report   Self-evaluation Report ( PDF )
  • 2008 Annual Research Report
  • 2007 Annual Research Report
  • Research Products

    (40 results)

All 2010 2009 2008 2007

All Journal Article (19 results) (of which Peer Reviewed: 19 results) Presentation (21 results)

  • [Journal Article] Production of hesperetin glycosides by Xanthomonas campestris and cyclodextrin glucanotransferase and their anti-allergic activities2010

    • Author(s)
      Kei Shimoda, Hiroki Hamada,
    • Journal Title

      Nutrients Vol.2

      Pages: 171-180

    • Related Report
      2010 Final Research Report
    • Peer Reviewed
  • [Journal Article] Enzymatic resolution of (RS)-1-phenylalkylβ-D-glucosides to (R)-1-phenylalkyl β-primeverosides and (S)-1-phenylalkyl β-D-glucosides via plant xylosyltransferase2010

    • Author(s)
      Kei Shimoda, Hisashi Katsuragi
    • Journal Title

      Tetrahedron: Asymmetry Vol.21

      Pages: 2060-2065

    • Related Report
      2010 Final Research Report
    • Peer Reviewed
  • [Journal Article] Production of Hesperetin Glycosides by Xanthomonas campestris and Cyclodextrin Glucanotransferase and Their Anti-allergic Activities2010

    • Author(s)
      Kei Shimoda, Hiroki Hamada
    • Journal Title

      Nutrients

      Volume: 2 Pages: 171-180

    • Related Report
      2010 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Enzymatic resolution of (RS)-1-phenylalkyl β-D-glucosides to (R)-1-phenylalkyl β-primeverosides and (S)-1-phenylalkyl β-D-glucosides via plant xylosyltransferase2010

    • Author(s)
      Kei Shimoda, Hisashi Katsuragi
    • Journal Title

      Tetrahedron : Asymmetry

      Volume: 21 Pages: 2060-2065

    • Related Report
      2010 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Glycosylation of fluorophenols by plant cell cultures2009

    • Author(s)
      Kei Shimoda, Naoji Kubota, Yoko Kondo,Daisuke Sato, Hiroki Hamada
    • Journal Title

      Int. J. Mol. Sci Vol.10

      Pages: 1942-1949

    • Related Report
      2010 Final Research Report
    • Peer Reviewed
  • [Journal Article] Glycosylation of Fluorophenols by Plant Cell Cultures2009

    • Author(s)
      下田恵, 久保田直治, 近藤陽子, 佐藤大介, 浜田博喜
    • Journal Title

      Int. J. Mol. Sci. 10巻

      Pages: 1942-1949

    • Related Report
      2009 Self-evaluation Report
    • Peer Reviewed
  • [Journal Article] Glycosylation of Fluorophenols by Plant Cell Cultures2009

    • Author(s)
      Kei Shimoda, Naoji Kubota, Yoko Kondo, Daisuke Sato, Hiroki Hamada
    • Journal Title

      Int.J.Mol.Sci. 10

      Pages: 1942-1949

    • Related Report
      2009 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Glycosylation of daidzin by the Eucalyptus cell cultures2008

    • Author(s)
      Kei Shimoda, Noriaki Sato, Tatsunari Kobayashi, Hatsuyuki Hamada, Hiroki Hamada
    • Journal Title

      Phytochemistry Vol.69

      Pages: 2303-2306

    • Related Report
      2010 Final Research Report
    • Peer Reviewed
  • [Journal Article] Synthesis of unnatural mono- and oligosaccharides of farnesol, geraniol, and (S)-perillyl alcohol by biocatalytic glycosylations2008

    • Author(s)
      Kei Shimoda, Sou Sakamoto, Nobuyoshi Nakajima, Hatsuyuki Hamada, Hiroki Hamada
    • Journal Title

      Chemistry Letters Vol.37

      Pages: 556-557

    • NAID

      10021080720

    • Related Report
      2010 Final Research Report
    • Peer Reviewed
  • [Journal Article] Synthesis of Unnatural Mono- and Oligosaccharides of Farnesol, Geraniol, and (S)-Perillyl Alcohol by Biocatalytic Glycosylations2008

    • Author(s)
      下田恵, 坂本創, 中島伸佳, 浜田初幸, 浜田博喜
    • Journal Title

      Chemistry Letters 37巻

      Pages: 556-557

    • NAID

      10021080720

    • Related Report
      2009 Self-evaluation Report
    • Peer Reviewed
  • [Journal Article] Glycosylation of Daidzin by the Eucalyptus Cell Cultures2008

    • Author(s)
      K. Shimoda, N. Sato, T. Kobayashi, H. Hamada, H. Hamada
    • Journal Title

      Phytochernisrry 69

      Pages: 2303-2306

    • Related Report
      2008 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Synthesis of Unnatural Mono-and Oligosaccharides of Farnesol, Geraniol and (S)-Perillyl Alcohol by Biocatalytic Glycosylations2008

    • Author(s)
      K. Shimoda, S. Sakamoto, N. Nakajima, H. Hamada, H. Hamada
    • Journal Title

      Chemistry Letters 37

      Pages: 556-557

    • NAID

      10021080720

    • Related Report
      2008 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Synthesis of curcumin β-maltooligosaccharides through biocatalytic glycosylation with Strophanthus gratus cell culture and cyclodextrin glucanotransferase2007

    • Author(s)
      Kei Shimoda, Takafumi Hara, HatsuyukiHamada, Hiroki Hamada
    • Journal Title

      Tetrahedron Letters Vol.48

      Pages: 4029-4032

    • Related Report
      2010 Final Research Report
    • Peer Reviewed
  • [Journal Article] Glycosylation of capsaicin and 8-nordihydorocapsaicin by cultured cells of Catharanthus roseus2007

    • Author(s)
      Kei Shimoda, Soonil Kwon, Akiko Utsuki, Shingo Ohiwa, Hisashi Katsuragi, Naoko Yonemoto, Hatsuyuki Hamada, Hiroki Hamada
    • Journal Title

      Phytochemistry Vol.68

      Pages: 1391-1396

    • Related Report
      2010 Final Research Report
    • Peer Reviewed
  • [Journal Article] Synthesis of α-tocopheryl disaccharides as potential antiallergic agents2007

    • Author(s)
      Kei Shimoda, Yoko Kondo, Masaaki Akagi, Koichi Abe, Hatsuyuki Hamada, Hiroki Hamada
    • Journal Title

      Chemistry Letters Vol.36

      Pages: 570-571

    • NAID

      10018881366

    • Related Report
      2010 Final Research Report
    • Peer Reviewed
  • [Journal Article] Synthesis of curcuminβ-maltooligosaccharides through biocatalytic glycosylation with Strophanthus gratus cell culture and cyclodextrin glucanotransferase2007

    • Author(s)
      下田恵, 原隆文, 浜田初幸, 浜田博喜
    • Journal Title

      Tetrahedron Letters 48巻

      Pages: 4029-4032

    • Related Report
      2009 Self-evaluation Report
    • Peer Reviewed
  • [Journal Article] Synthesis of curcumin β-maltooligosaccharides through biocatalytic glycosylation with Strophanthus gratus cell culture and cyclodextrin glucanotransferase2007

    • Author(s)
      Kei Shimoda
    • Journal Title

      Tetrahedron Letters 48

      Pages: 4029-4032

    • Related Report
      2007 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Glycosylation of capsaicin and 8-nordihydorocapsaicin by cultured cells of Catharanthus roseus2007

    • Author(s)
      Kei Shimoda
    • Journal Title

      Phytochemistry 68

      Pages: 1391-1396

    • Related Report
      2007 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Synthesis of α-tocopheryl disaccharides as potential antiallergic agents2007

    • Author(s)
      Kei Shimoda
    • Journal Title

      Chemistry Letters 36

      Pages: 570-571

    • NAID

      10018881366

    • Related Report
      2007 Annual Research Report
    • Peer Reviewed
  • [Presentation] 植物由来糖転移酵素を活用した高機能性配糖体の合成2010

    • Author(s)
      浜田博喜,小原隆博,山本涼平,下田恵,小崎紳一,中山亨,葛城寿史
    • Organizer
      第52回天然有機化合物討論会
    • Related Report
      2010 Final Research Report
  • [Presentation] The effective synthesis of the lead compounds of the drug development and food supplement-Glycosylation of flavanoids using plant cultured cells2010

    • Author(s)
      Hiroki Hamada, Kei Shimoda, Nobuyoshi Nakajima
    • Organizer
      環太平洋国際化学会議PACIFICHEM2010
    • Related Report
      2010 Final Research Report
  • [Presentation] 植物由来糖転移酵素を活用した高機能性配糖体の合成2010

    • Author(s)
      浜田博喜, 小原隆博, 山本涼平, 下田恵, 小崎紳一, 中山亨, 葛城寿史
    • Organizer
      第52回天然有機化合物討論会
    • Place of Presentation
      静岡
    • Related Report
      2010 Annual Research Report
  • [Presentation] The effective synthesis of the lead compounds of the drug development and food supplement-Glycosylation of flavanoids using plant cultured cells2010

    • Author(s)
      Hiroki Hamada, Kei Shimoda, Nobuyoshi Nakajima
    • Organizer
      環太平洋国際化学会議 PACIFICHEM2010
    • Place of Presentation
      ハワイ
    • Related Report
      2010 Annual Research Report
  • [Presentation] Glycosylation of biological active compound using plant cultured suspention cells2009

    • Author(s)
      浜田博喜, 大広あずさ, 木村江利子, 近藤舞, 佐藤大介, 中島伸佳, 下田恵
    • Organizer
      Plant Biology 2009
    • Place of Presentation
      ハワイ
    • Year and Date
      2009-07-18
    • Related Report
      2009 Annual Research Report 2009 Self-evaluation Report
  • [Presentation] 植物酵素触媒によるワンステップグリコシル化反応2009

    • Author(s)
      浜田博喜, 大広あずさ, 木村江利子, 近藤舞, 佐藤大介, 下田恵
    • Organizer
      第95回有機合成シンポジウム
    • Place of Presentation
      慶応義塾大学
    • Year and Date
      2009-06-10
    • Related Report
      2009 Self-evaluation Report
  • [Presentation] 植物酵素触媒によるワンステップグリコシル化反応2009

    • Author(s)
      濱田博喜, 大広あずさ, 木村江利子, 近藤舞, 佐藤大介, 下田恵
    • Organizer
      第95回有機合成シンポジウム
    • Place of Presentation
      慶応大学
    • Year and Date
      2009-06-10
    • Related Report
      2009 Annual Research Report
  • [Presentation] 植物培養細胞を用いたフラバノン類の変換-水酸化と配糖化2009

    • Author(s)
      山本涼平, 小林達成, 比嘉望, 下田恵, 中島伸佳, 浜田博喜
    • Organizer
      日本化学会第89回春季年会
    • Place of Presentation
      日本大学
    • Year and Date
      2009-03-29
    • Related Report
      2008 Annual Research Report
  • [Presentation] 植物培養細胞によるモノテルペン類の配糖化2009

    • Author(s)
      小林達成, 佐藤大介, 下田恵, 久保田直治, 浜田博喜
    • Organizer
      日本化学会第89回春季年会
    • Place of Presentation
      日本大学
    • Year and Date
      2009-03-29
    • Related Report
      2008 Annual Research Report
  • [Presentation] 辛くない唐辛子とブドウポリフェノールの機能解明2009

    • Author(s)
      浜田博喜, 大広あすさ, 下田恵, 本間知夫
    • Organizer
      日本化学会第89回春季年会
    • Place of Presentation
      日本大学
    • Year and Date
      2009-03-29
    • Related Report
      2008 Annual Research Report
  • [Presentation] 植物酵素触媒によるワンステップグリコシル化反応2009

    • Author(s)
      濱田博喜,大広あずさ,木村江利子,近藤舞,佐藤大介, 下田恵
    • Organizer
      第95回有機合成シンポジウム
    • Related Report
      2010 Final Research Report
  • [Presentation] Glycosylation of biological active compound using plant cultured suspention cells2009

    • Author(s)
      Hiroki Hamada,Azusa Ohiro,Eriko Kimura,Mai Kondo,Daisuke Sato,Nobuyosi Nakajima, Kei Shimoda
    • Organizer
      Plant Biology 2009
    • Related Report
      2010 Final Research Report
  • [Presentation] 生体触媒を活用した有用物質の生産2008

    • Author(s)
      浜田博喜
    • Organizer
      日本化学会第88回春季年会
    • Place of Presentation
      立教大学
    • Year and Date
      2008-03-28
    • Related Report
      2007 Annual Research Report
  • [Presentation] 植物培養細胞によるモノテルペンの配糖化2008

    • Author(s)
      浜田博喜
    • Organizer
      日本化学会第88回春季年会
    • Place of Presentation
      立教大学
    • Year and Date
      2008-03-27
    • Related Report
      2007 Annual Research Report
  • [Presentation] 植物培養細胞によるレスベラトロールの配糖化2008

    • Author(s)
      小林達成
    • Organizer
      日本化学会第88回春季年会
    • Place of Presentation
      立教大学
    • Year and Date
      2008-03-27
    • Related Report
      2007 Annual Research Report
  • [Presentation] 植物培養細胞を用いたフラバノン類の変換-水酸化と配糖化2008

    • Author(s)
      山本涼平,小林達成,比嘉望,下田恵,中島伸佳,浜田博喜
    • Organizer
      日本化学会第89回春季年会
    • Related Report
      2010 Final Research Report
  • [Presentation] 植物培養細胞によるモノテルペン類の配糖化2008

    • Author(s)
      小林達成,佐藤大介,下田恵,久保田直冶,浜田博喜
    • Organizer
      日本化学会第89回春季年会
    • Related Report
      2010 Final Research Report
  • [Presentation] 辛くない唐辛子とブドウポリフェノールの機能解明2008

    • Author(s)
      浜田博喜,大広あずさ,下田恵,本間知夫
    • Organizer
      日本化学会第89回春季年会
    • Related Report
      2010 Final Research Report
  • [Presentation] 植物培養細胞によるモノテルペンの配糖化2007

    • Author(s)
      浜田博喜,小林達成,佐藤大介,下田恵
    • Organizer
      日本化学会第88回春季年会
    • Related Report
      2010 Final Research Report
  • [Presentation] 植物培養細胞によるレスベラトロールの配糖化2007

    • Author(s)
      小林達成,大広あずさ,石原浩二,中島伸佳,下田恵,浜田博喜
    • Organizer
      日本化学会第88回春季年会
    • Related Report
      2010 Final Research Report
  • [Presentation] 生体触媒を活用した有用物質の生産2007

    • Author(s)
      浜田博喜,小林達成,下田恵
    • Organizer
      日本化学会第88回春季年会
    • Related Report
      2010 Final Research Report

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Published: 2007-04-01   Modified: 2016-04-21  

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