| Project/Area Number |
12660097
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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 |
Bioproduction chemistry/Bioorganic chemistry
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| Research Institution | Nagoya University |
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Principal Investigator |
ICHIKAWA Yoshiyasu NagoyaUniversity, School of Agricultural Sciences, 農学部, 助教授 (60193439)
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| Co-Investigator(Kenkyū-buntansha) |
ISOBE Minoru NagoyaUniversity, School of Agricultural Sciences, 農学部, 教授 (00023466)
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| Project Period (FY) |
2000 – 2001
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| Project Status |
Completed (Fiscal Year 2001)
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| Budget Amount *help |
¥3,400,000 (Direct Cost: ¥3,400,000)
Fiscal Year 2001: ¥1,000,000 (Direct Cost: ¥1,000,000)
Fiscal Year 2000: ¥2,400,000 (Direct Cost: ¥2,400,000)
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| Keywords | nucleoside antibiotics / blustiadins / puptide hucleic aird / inhibitor / DNA / cytosinine / siginatvopy / allyl cyanate / アリルシアナ-ト |
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| Research Abstract |
Blasticidin S was isolated from Streptomyces gmeochromogenes and at one time was used as a fungicide for the Prevention of nee blast in Japan. Careful acid hydrolysis of blasticidin S yielded blastidic acid and cytosinine Structurally, cytosinine is charactenzed as a peculiar nucleoside possessing (3-amino acid functionality ; and this structural feature inspired us to propose a new type of DNA-analogue based on a peptide backbone (peptidenucleoside, PNA). With this end in mind, we here focused our attention on'the synthesis of blasticidin S.
The synthesis of Boc-protected blastidic acid was achieved in 9 steps starting from chiral carboxylic acid AIM cyanate-to-isocyanate rearrangement has been successfully employed for the construction of an unsaturated amino sugar moiety of cytosmme, and our synthesis of the fully protected cytosinine derivative required 13 steps starting from 2-acetoxy-tn-O-acetyl-D-glucal. Further studies toward the total synthesis of blasticidin S are now underway in our laboratory.
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