1995 Fiscal Year Final Research Report Summary
Complete Structure Elucidation of Maitotoxin
| Project/Area Number |
06453211
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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 |
Bioorganic chemistry
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| Research Institution | The University of Tokyo |
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Principal Investigator |
MURATA Michio The University of Tokyo, Graduate School of Science, Associate Professor, 大学院・理学系研究科, 助教授 (40183652)
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| Co-Investigator(Kenkyū-buntansha) |
SASAKI Makoto The University of Tokyo, Graduate School of Science, Research Associate, 大学院・理学系研究科, 助手 (80235267)
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| Project Period (FY) |
1994 – 1995
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| Keywords | maitotoxin / marine natural products / polyether / dinoflagellate / NMR / spin coupling constants / stereoselective synthesis / absolute stereochemistry |
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| Research Abstract |
Maitotoxin is the most toxic and largest natural product among non-biopolymers known to date. Althought most of stereogenic centers in ring systems was assigned by simple NOE experiments, the complete structural elucidation was hampered by the presence of asymmetric centers in acyclic portions, particularly, C1-C14 and C134-C142 side chains. The present study has successfully elucidated the total sturcture by menas of NMR spectroscopy coupled with stereoselective synthesis of the fragmental structures. In the NMR analysis, we focused on the carbon-proton copling constants, which provided important dihedral angles for the conformational and configurational assignments of the side chains. The absolute stereochemistry has been also assigned by the synthesis of all the possible stereoisomer for fragment C,which was generated by periodate degradation of maitotoxin.
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