ID | 19875 |
Eprint ID | 19875
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FullText URL | |
Title Alternative | Identification of Ornithine-lactam Converted from Arginine in Streptomyces incarnatus NRRL8089
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Author |
Fukuda, Koji
Inagaki, Kenji
Kaken ID
researchmap
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Abstract | Sinefungin is a nucleoside antibiotic, in which a molecule of L-ornithine is linked to the 5' end of adenosine through a C-C bond. The antibiotic was isolated from the culture broth of Streptomyces incarnatus. For the purpose of detecting intermediate of sinefungin biosynthesis, resting cell suspensions were incubated with supplemental L-arginine, and L-ornithine. 50mM Arginine was converted to a compound X that has low polarity. 50mM ornithine was not converted and remained in reaction solution. Compound X was purified using HPLC, and analyzed using (1)H-NMR and FAB-MS. These analyses showed that a compound X is "ornithine-lactam" (Mw=114), which has a structure of circularized ornithine. These results indicated that S. incarnatus has an enzyme that converts arginine to ornithine-lactam. Such an enzyme has never been reported, and suggested that it may be relevant to sinefungin biosynthesis.
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Abstract Alternative | シネフンギンは抗真菌,抗マラリア活性を有する核酸系抗生物質であり,放線菌 S. incarnatus により生合成される.シネフンギンはアデノシンとオルニチンがCンC結合した構造であり,無細胞抽出液での取り込み実験からLンアルギニンと ATP から生合成されると推測される.Lンアルギニン,Lンオルニチンを S. incarnatus の休止菌体反応系への投与を行いシネフンギン中間体の探索を行った.その結果50ヒアルギニンは24時間以内に低極性化合物へと変換された.一方50ヒオルニチンは変換されず反応液中に残存した.HPLC で化合物を精製し,1HンNMR,FABンMS での分析の結果オルニチン環状モノペプチド,「オルニチンラクタム」(分子量114)であることを明らかにした.この結果は S. incarnatus がアルギニンからオルニチンラクタムへの変換酵素を有する事を示唆する.このような酵素の報告例はこれまでになく,ニ次代謝酵素であることが示唆され,シネフンギン生合成との関連性に興味が持たれる.
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Keywords | sinefungin
arginine
ornithine
Streptomyces
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Published Date | 2010-02-01
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Publication Title |
岡山大学農学部学術報告
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Publication Title Alternative | Scientific Reports of the Faculty of Agriculture Okayama University
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Volume | volume99
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Issue | issue1
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Publisher | 岡山大学農学部
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Publisher Alternative | Faculty of Agriculture, Okayama University
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Start Page | 1
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End Page | 5
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ISSN | 0474-0254
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NCID | AN00033029
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Content Type |
Departmental Bulletin Paper
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language |
Japanese
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File Version | publisher
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Refereed |
False
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Eprints Journal Name | srfa
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