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Syntheses and Cytokinin Activities of the 1'-or 1"-Methyl Derivatives in the Zeatin and IPA Families.

Research Project

Project/Area Number 04453152
Research Category

Grant-in-Aid for General Scientific Research (B)

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

Principal Investigator

FUJII Tozo  Professor, Faculty of Pharmaceutical Sciences, Kanazawa Univaersity, 薬学部, 教授 (20019649)

Co-Investigator(Kenkyū-buntansha) MATSUBARA Satoshi  Professor, Faculty of Living Sciences, Kyoto Prefectural University, 生活科学部, 教授 (80046458)
OHBA Masashi  Assistant, Faculty of Pharmaceutical Sciences, Kanazawa University, 薬学部, 助手 (60115219)
Project Period (FY) 1992 – 1993
Project Status Completed (Fiscal Year 1993)
Budget Amount *help
¥6,900,000 (Direct Cost: ¥6,900,000)
Fiscal Year 1993: ¥1,800,000 (Direct Cost: ¥1,800,000)
Fiscal Year 1992: ¥5,100,000 (Direct Cost: ¥5,100,000)
KeywordsCytokinin / Phytohormone / Zeatin derivative / IPA derivative / alpha-Amino aldehyde / Purinylation / Tobacco callus bioassay / Lettuce seed germination bioassay / Wittig反応
Research Abstract

1. The first chiral synthesis of 2-hydroxy-1'-methyl-trans-zeatin (1)has been accomplished. The systhesis started from D-or L-alanine and proceeded through an alpha-amino aldehyde/olefination route to give[R-(E)]-or[S-(E)]-4-amino-2-methyl-2-penten-1-ol ethanedioate [(R)-2 or (S)-2]. Condensations of 2-hydroxy-6methylthiopurine with (R)-2 and (S)-2 furnishied (1'R)-1 and (1'S)-1, respectively. As a result or this synthesis, the gross structure of a marine green alga cytokinin was established to be 1.
2. In a similar manner, [R-(Z)]-and [S-(Z)]-4-amino-2-methyl-2-penten-1-ol ethanedioates [(R)-3 and (S)-3] were prepared from D- and L-alanine, respectively. Condensations of (R)-3 and (S)-3 with 6-chloropurine or its 9-riboside gave (1'R)-and (1'S)-1'-methyl-cis-zeatins [(1'R)-4 and (1'S)-4] or their 9-ribosides [(1"R)-5 and (1"S)-5].
3. Both enantiomers [(1'R)-6 and (1'S)-6] of N^6-(1,3-dimethyl-2-butenyl)adenine (6) and their 9-ribosides [(1"R)-7 and (1"S)-7] were synthesized via analogous routes.
4. A novel synthesis of cis-zeatin was achieved through an alpha-amino aldehyde/olefination route, which was also applied successfully to the synthesis of 9-(2-deoxy-beta-D-ribofuranosyl)-cis-zeatin(8).
5. The above 1'-or 1"-methylated derivatives [(1'R)-1, (1'S)-1, (1'R)-4, (1'S)-4, (1"R)-5, (1"S)-5, (1'R)-6, (1'S)-6, (1"R)-7. (1"S)-7. amd 8] of the zeatin and IPA families were tested for cytokinin activity in the tobacco callus and the lettuce seed germination bioassays to discuss their structure-activity relationships.

Report

(3 results)
  • 1993 Annual Research Report   Final Research Report Summary
  • 1992 Annual Research Report
  • Research Products

    (9 results)

All Other

All Publications (9 results)

  • [Publications] Antonio Evidente: "Syntheses of cis-Zeatin and Its 9-(2-Deoxy-β-D-ribofuranosyl) Derivative:A Novel Stnthetic Route to the Side Chain at C(6),and Cytokinin Activity." Chem.Pharm.Bull.40. 1937-1939 (1992)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1993 Final Research Report Summary
  • [Publications] Tozo Fujii: "Purines.LV.Syntheses and Cytokinin Activities of Some Adenine and Adenosine Derivatives Related to 1'-Methylzeatin." Chem.Pharm.Bull.41. 1362-1365 (1993)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1993 Final Research Report Summary
  • [Publications] Tozo Fujii: "Purines.LXII.Both Enantiomers of N^6-(1,3-Dimethyl-2-butenyl)adenine and Their 9-β-D-Ribofuranosides:Synthesis and Cytokinin Activity. (印刷中)" Chem.Pharm.Bull.42. (1994)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1993 Final Research Report Summary
  • [Publications] Satoshi Matsubara: "Cytokinin Activities of 1'-Methyl Derivatives of Zeatin N^6-(Δ^2-Isopentenyl)adenine and of Their 9-β-D-Ribofuranosides in Lettuce Seed Germination. (印刷中)" Sci.Rep.Kyoto Pref.Univ.45. (1994)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1993 Final Research Report Summary
  • [Publications] Antonio Evidente, Gennaro Piccialli, Angelo Sisto, Masashi Ohba, Kei Honda, and Tozo Fujii: ""Syntheses of cis-Zeatin and Its 9-(2-Deoxy-beta-D-ribofuranosyl) Derivative : A Novel Synthetic Route to the Side Chain at C(6), and Cytokinin Activity"" Chem.Pharm.Bull.40. 1937-1939 (1992)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1993 Final Research Report Summary
  • [Publications] Tozo Fujii, Masashi Ohba, Hitoshi Kawamura, Tsuyoshi Haneishi, and Satoshi Matsubara: ""Purines. LV.Syntheses and Cytokinin Activities of Some Adenine and Adenosine Derivatives Related to 1'-Methylzeatin"" Chem.Pharm.Bull.41. 1362-1365 (1993)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1993 Final Research Report Summary
  • [Publications] Tozo Fujii, Masashi Ohba, Hitoshi Kawamura, Yoshiyuki Nakashio, Kei Honda, and Satoshi Matsubara: ""Purines. LXII.Both Enantiomers of N^6-(1,3-Dimethyl-2-butenyl) adenine and Their 9-beta-D-Ribofuranosides : Synthesis and Cytokinin Activity"" Chem.Pharm.Bull.42(6), (in press). (1994)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1993 Final Research Report Summary
  • [Publications] Satoshi Matsubara, Tozo Fujii, and Masashi Ohba: ""Cytokinin Activities of 1'-Methyl Derivatives of Zeatin and N^6-(DELTA^2-Isopentenyl) adenine and of Their 9-beta-D-Ribofuranosides in Lettuce Seed Germination"" Sci.Rep.Kyoto Pref.Univ.45, (in press). (1994)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1993 Final Research Report Summary
  • [Publications] Antonio Evidente: "Syntheses of cis-Zeatin and Its 9-(2-Deoxy-β-D-ribofuranosyl)Derivative:A Novel Synthetic Route to the Side Chain at C(6) and Cytokinin Activity" Chem.Pharm.Bull.,. 40. 1937-1939 (1992)

    • Related Report
      1992 Annual Research Report

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Published: 1992-04-01   Modified: 2016-04-21  

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