2008年3月
TMG-chitotriomycin, an enzyme inhibitor specific for insect and fungal beta-N-acetylglucosaminidases, produced by actinomycete Streptomyces anulatus NBRC 13369
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
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- 巻
- 130
- 号
- 12
- 開始ページ
- 4146
- 終了ページ
- 4152
- 記述言語
- 英語
- 掲載種別
- 研究論文(学術雑誌)
- DOI
- 10.1021/ja077641f
- 出版者・発行元
- AMER CHEMICAL SOC
A novel beta-N-acetylglucosaminidase (GIcNAcase) inhibitor named TMG-chitotriomycin (1) was isolated from the culture filtrate of Streptomyces anulatus NBRC13369. The strain produced 1 only when colloidal chitin was used as the sole carbon source in the production medium. The structure of 1 was determined by spectral and constitutive sugar analyses of the corresponding alditol derivatives to be an equilibrated mixture of alpha-D-N,N,N-triMeGIcNH(2)-(1,4)-beta-D-GIcNAc-(1,4)-beta-D-GIcNAc-(1,4)-D-GlcNAc and its C-2 epimer of the reducing end residue. TMG-chitotriomycin (1) showed potent and selective inhibition of insect and fungal GIcNAcases with no inhibition of mammalian and plant GIcNAcases. In contrast, the known GIcNAcase inhibitor nagstatin potently inhibited all GIcNAcases. It should be emphasized that synthesized D-N,N,N-triMeGIcNH(2), which is the component sugar of 1, showed no inhibition of the insect Spodoptera litura GIcNAcase. These results suggest that the (GIcNAc)(3) unit positioned at the reducing end of 1 is essential for its enzyme inhibitory activity. The unique inhibitory spectrum of 1 will be useful to study chitinolytic systems and to develop selective fungicides or pesticides.
- リンク情報
- ID情報
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- DOI : 10.1021/ja077641f
- ISSN : 0002-7863
- Web of Science ID : WOS:000254173600079