ISONITRILES FROM THE BLUE-GREEN-ALGA SCYTONEMA-MIRABILE
ISONITRILES FROM THE BLUE-GREEN-ALGA SCYTONEMA-MIRABILE
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DOI：
10.1021/jo00301a041
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发表时间：
1990-07-06
影响因子：
3.6
通讯作者：
SUZUKI, M
中科院分区：
文献类型：
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作者：
CARMELI, S;MOORE, RE;SUZUKI, M
已发现一种命名为BY-8-1号菌株的奇异Scytonema mirabile（迪尔温）Bornet的气生型含有六种新的异腈，即奇异烯异腈A-F（7-12），它们具有轻微的细胞毒性和抗微生物性。通过详细的光谱分析确定了7-12的总体结构。通过化学降解和降解产物与合成样品的直接比较，解决了7-12的相对和绝对立体化学;例如，mirabilene-A异腈（7）被降解为甲基（3R，5 R，7S，9 S）-3，5，7，9-四甲氧基-10-氧代十一醛（15）和（S）-3-三氟乙酰氨基丁酸异丙酯（14），表明C-4，7例C-6、C-8、C-10、C-16均为S。
An aerial form of Scytonema mirabile (Dillwyn) Bornet, designated strain number BY-8-1, has been found to contain six novel isonitriles, viz. mirabilene isonitriles A-F (7-12), which are mildly cytotoxic and antimicrobial. The gross structures of 7-12 were determined by detailed spectral analysis. The relative and absolute stereochemistry of 7-12 were solved by chemical degradation and direct comparison of degradation products with synthetic samples; mirabilene-A isonitrile (7), for example, was degraded to methyl (3R,5R,7S,9S)-3,5,7,9-tetramethyloxy-10-oxoundecanal (15) and isopropyl (S)-3-trifluoroacetamidobutyrate (14), which indicated that the absolute configurations of C-4, C-6, C-8, C-10, and C-16 in 7 were all S.