SYNTHESIS AND STEREOCHEMISTRY OF INDOLACTAM-V, AN ACTIVE FRAGMENT OF TELEOCIDINS - STRUCTURAL REQUIREMENTS FOR TUMOR-PROMOTING ACTIVITY
SYNTHESIS AND STEREOCHEMISTRY OF INDOLACTAM-V, AN ACTIVE FRAGMENT OF TELEOCIDINS - STRUCTURAL REQUIREMENTS FOR TUMOR-PROMOTING ACTIVITY
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DOI：
10.1016/s0040-4020(01)96073-9
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发表时间：
1986-01-01
期刊：
影响因子：
2.1
通讯作者：
SAKAI, S
中科院分区：
文献类型：
--
作者：
ENDO, Y;SHUDO, K;SAKAI, S
（-）-Indolactam-V是强效肿瘤促进剂teleocidins的活性片段，也已被分离为轮枝链霉菌代谢物，它是从4-硝铵开始合成的。（-）-吲哚内酰胺-V的绝对立体化学为（9 S，12 S），表明teleocidin及其相关化合物是由L-氨基酸生物合成的。还合成了三种非天然非对映异构体。（-）-和（.+.）-的NMR谱吲哚内酰胺-V及其衍生物在溶液中以两种构象状态存在。根据化学位移、偶合常数和核Overhauser效应，推测这两种构象异构体的结构分别为SOFA和TWIST型，其特征分别为反式和顺式酰胺键。两种构象异构体的计算比例与观察到的比例一致。
(-)-Indolactam-V, which is an active fragment of the potent tumor promoters teleocidins and has also been isolated as a Streptoverticillium metabolite, has been synthesized starting from 4-nitrogramine. The absolute stereochemistry of (-)-indolactam-V has been determined to be (9S, 12S), which suggest that teleocidins and related compounds are biosynthesized from L-amino acids. Three unnatural diastereoisomers were also synthetized. The NMR spectra of (-)- and (.+-.)-indolactam-V and its derivatives showed that they exist in two conformational states in solution. The structures of the two conformers were deduced from the chemical shifts, coupling constants and nuclear Overhauser effects to be SOFA and TWIST form which are characterized by trans and cis amide bonds, respectively. The calculated ratio of the two conformers was consistent with the observed ratio.