BIOSYNTHESIS OF PSEUROTIN-A
BIOSYNTHESIS OF PSEUROTIN-A
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DOI：
10.1016/0040-4020(81)85056-9
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发表时间：
1981-01-01
期刊：
影响因子：
2.1
通讯作者：
TAMM, C
中科院分区：
文献类型：
--
作者：
MOHR, P;TAMM, C
测定并分析了卵状假尿草次生代谢产物假黄素A(1)及其衍生物的13C-NMR谱。与[1,2- 13c2]-丙酸、[2- 13c]-丙二酸、[1- 13c]-苯丙氨酸、[2,3- 13c2]-苯丙氨酸和[13C-CH3]- l -蛋氨酸结合实验表明，1的组成单元为1个丙酸（起始单元）、4个丙二酸、1个苯丙氨酸和2个蛋氨酸。提出了一种生物遗传学途径。用[13C2H3]- l -蛋氨酸进行的实验表明，O-甲基化和c -甲基化发生时，甲基的所有3个H原子都保留了下来。以[2-13C2H2]-丙酸盐为前体，得到。对启动单元的-H原子进行了研究。最后用质谱法和13C核磁共振谱法测定了[2-13C， 15N]-苯丙氨酸的掺入率。通过与加入[15N]-苯丙氨酸后得到的标记结果进行比较，可以推断15N原子不具有统计分布。因此，可以排除无氮中间体。
The 13C-NMR spectra of pseurotin A (1), a secondary metabolite of Pseudeurotium ovalis Stolk, and of some derivatives were measured and interpreted. Incorporation experiments with [1,2-13C2]-propionate, [2-13C]-malonate, [1-13C]- and [2,3-13C2]-phenylalanine and [13C-CH3]-L-methionine showed that the building blocks of 1 are 1 unit of propionate (starter unit), 4 units of malonate, 1 unit of phenylalanine and 2 units of methionine. A biogenetic pathway is proposed. Experiments with [13C2H3]-L-methionine demonostrated that O- and C-methylation occur with retention of all 3 H atoms of the methyl group. Using [2-13C2H2]-propionate as precursor, the fate of the .alpha.-H atoms of the starter unit was studied. Finally, the incorporation rates with [2-13C, 15N]-phenylalanine were determined by mass spectrometry and 13C NMR spectroscopy. By comparing the labeling pattern with the results obtained after the incorporation of [15N]-phenylalanine, it could be deduced that the 15N atoms are not statistically distributed. Hence, a N-free intermediate can be excluded.