| Project/Area Number |
11672122
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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 | Kanazawa University |
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Principal Investigator |
TAMURA Osamu Kanazawa University, Faculty of Pharmaceutical Science, 薬学部, 助教授 (30257141)
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| Co-Investigator(Kenkyū-buntansha) |
SAKAMOTO Masanori Meiji Pharmaceutical University, 薬学部, 教授 (70087774)
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| Project Period (FY) |
1999 – 2001
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| Project Status |
Completed (Fiscal Year 2001)
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| Budget Amount *help |
¥2,800,000 (Direct Cost: ¥2,800,000)
Fiscal Year 2001: ¥600,000 (Direct Cost: ¥600,000)
Fiscal Year 2000: ¥800,000 (Direct Cost: ¥800,000)
Fiscal Year 1999: ¥1,400,000 (Direct Cost: ¥1,400,000)
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| Keywords | nikkomycin Bz / α-alkoxycarbonylnitrone / (5S)-5.6-dihydro-5-phenyl-2H-1.4-oxazin-2-one N-oxide / carbocyclic polyoxin C / polyoxin C / N-terminal amino acid / b-substitued a-amino acids / clavalanine / (5S)-5,6-dihydro-5-pheny1-2H-1,4-oxazin-2-one N-ox / 多官能性 / nikkomycyn Bz / carbocyclic polyoxin C / 環状ニトロン / エステル交換 / アリルアルコール / 分子軌道計算 / ニトロン / 付加反応 / キレート / マグネシウムブロミド / 環化付加反応 / clavalanin |
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| Research Abstract |
Nikkomycin Bz, a dipeptide antibiotic, posseses γ-hydroxy-α-amino acid as the N-terminal amino acid and a nucleoside amino acid as the C-terminal amino acid.
1) α-Allyloxycarbonylnitrone having a sugar auxiliary was explored. Using this method, the N-terminal amino acid moiety was synthesized.
2) (5R) [and (5S)]-5,6-Dihydro-5-phenyl-2H-1, 4-oxazin-2-one N-oxides were designed and synthesized as the chiral (E)-geometry-fixed α-alkoxycarbonylrtitrones. The key intermediate of carbocy polyoxin C, the carbocyclic analogue of the C-terminal amino acid, was synthesized by employing 1,3-dipolar cycloaddition of the cyclic nitrone.
3) Nucleophilic addition reaction of 2-trimethylsilyloxyfurah to N-Gulosyi-C-alkoxymetnyl-nitrones was explored. The key intermediate of polyoxin C, the C-terminai amino acid of nikkomycin Bz, was synthesized by employing this method.
4) Methods mentioned above were applied to the synthesis of highly functionalized anti- and syn-β-substituted α-amino acids.
5) Highly stereoselective cycloaddition of (5S)-5,6-dihydro-5-phenyl-2H-1 ,4-oxazin-2-one N-oxide with allyll alcohol in the presence of MgBr_2 was applied to the synthesis of an antibiotic clavalanine.
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