| Project/Area Number |
10672002
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| Research Category |
Grant-in-Aid for Scientific Research (C)
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| Allocation Type | Single-year Grants |
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| Section | 一般 |
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| Research Field |
Chemical pharmacy
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| Research Institution | Toho University |
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Principal Investigator |
AKITA Hiroyuki Toho University-School of Pharmaceutical Sciences, Professor, 薬学部, 教授 (60087525)
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| Co-Investigator(Kenkyū-buntansha) |
NOZAWA Masako Assistant, 薬学部, 助手 (10277345)
KATO Keisuke Instructor, 薬学部, 講師 (80276609)
ONO Machiko Associated professor, 薬学部, 助教授 (80104149)
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| Project Period (FY) |
1998 – 1999
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| Project Status |
Completed (Fiscal Year 1999)
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| Budget Amount *help |
¥2,600,000 (Direct Cost: ¥2,600,000)
Fiscal Year 1999: ¥600,000 (Direct Cost: ¥600,000)
Fiscal Year 1998: ¥2,000,000 (Direct Cost: ¥2,000,000)
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| Keywords | Macrosphelide A / Chuangxinmycin / (-)-Ambrox / (+)-Zonarol / Nikkomycin B / Vitamin E / lipase / Total synthesis / 抗生物質 / chuangxinmycin / Nikkoroycin B |
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| Research Abstract |
In this scientific program, asymmetric syntheses of bioactive compounds possessing inhbition activity of cell-adhesion and antitumour activity were carried out based on enzymatic function.
1. Total synthesis of macrosphelide A possessing inhibition activity of cell-adhesion was achieved based on enzymatic function. The key chiral intermediate, methyl (4R,5S)-5-acetoxy-4-benzyloxy-(2E)-hexenoate was obtained by the enantioselective hydrolysis using lipase of the corresponding racemate.
2. Total synthesis of (-)-chuangxinmycin having antimicrobial activity was achieved based on the reaction of 4-iodoindole and methyl (2R,3S)-epoxy butanoate. This chiral intermediate was also obtained based on the enantioselective hydrolysis using lipase of the racemic (2,3)-trans-2-acetoxy-3-chloro butanoate.
3. The synthesis of decalin type chiral synthon possessing decahydro-5,5,8a-trimethyl-naphthalene skeleton was achieved based on enzymatic function. Thus obtained chiral synthons were converted into (-)-ambrox bearing a powerful amber-type aroma and marine natural product, (+)-zonarol.
4. Asymmetric syntheses of peptidyl nucleoside antibiotic, nikkomycin B and vitamin E were also achieved based on enzymatic function.
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