INVESTIGATIONS OF THE BIOSYNTHESIS AND STRUCTURAL REVISION OF LANDOMYCIN-A
INVESTIGATIONS OF THE BIOSYNTHESIS AND STRUCTURAL REVISION OF LANDOMYCIN-A
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DOI：
10.1021/jo00094a037
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发表时间：
1994-07-29
影响因子：
3.6
通讯作者：
BEALE, JM
中科院分区：
文献类型：
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作者：
WEBER, S;ZOLKE, C;BEALE, JM
用[1-C-13]-、[1，2-C-13（2）]-和[1-C-13，O-18（2）]乙酸盐进行的补料实验以及在富含O-18的气氛下进行的发酵，得到了关于土地霉素A糖苷配基部分的所有碳和氧原子的生物合成来源以及十酮肽链掺入方向的信息。兰霉素酮中的六个氧中只有两个似乎来自乙酸酯结构单元。这就对目前关于多环芳香聚酮化合物形成的假说提出了质疑。在生物合成的早期提出了一些不寻常的前芳香脱氧步骤。作为生物合成研究的另一个结果，修改了兰霉素A的结构，从而修改了所有其他兰霉素的结构，将酚-糖苷连接的脱氧糖链的位置从2修改为1。
Feeding experiments with [1-C-13]-, [1,2-C-13(2)]-, and [1-C-13,O-18(2)]acetate as well as a fermentation under an O-18-enriched atmosphere resulted in information regarding the biosynthetic origin of all carbon and of the oxygen atoms of the landomycin A aglycon moiety as well as of the direction of the incorporation of the decaketide chain. Only two of the six oxygens in landomycinone seem to originate from the acetate building blocks. This raises questions about current hypotheses for the formation of multicyclic aromatic polyketides. Some unusual prearomatic deoxygenation steps early in the biosynthesis have been proposed. As an additional result of the biosynthetic investigations, the structure of landomycin A and thus of all other landomycins were revised concerning the position of the phenol-glycosidically linked deoxysaccharide chain from 2 to 1.