1993 Fiscal Year Final Research Report Summary
Syntheses and Cytokinin Activities of the 1'-or 1"-Methyl Derivatives in the Zeatin and IPA Families.
| Project/Area Number |
04453152
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| Research Category |
Grant-in-Aid for General Scientific Research (B)
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| Allocation Type | Single-year Grants |
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| Research Field |
Chemical pharmacy
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| Research Institution | Kanazawa University |
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Principal Investigator |
FUJII Tozo Professor, Faculty of Pharmaceutical Sciences, Kanazawa Univaersity, 薬学部, 教授 (20019649)
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| 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)
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| Project Period (FY) |
1992 – 1993
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| Keywords | Cytokinin / Phytohormone / Zeatin derivative / IPA derivative / alpha-Amino aldehyde / Purinylation / Tobacco callus bioassay / Lettuce seed germination bioassay |
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| 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.
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