Eight-Membered Ring-Containing Jadomycins: Implications for Non-enzymatic Natural Products Biosynthesis
Eight-Membered Ring-Containing Jadomycins: Implications for Non-enzymatic Natural Products Biosynthesis
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DOI：
10.1021/ja5114672
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发表时间：
2015-03-11
影响因子：
15
通讯作者：
Jakeman, David L.
中科院分区：
文献类型：
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作者：
Robertson, Andrew W.;Martinez-Farina, Camilo F.;Jakeman, David L.
Jadomycin Oct (1) 是从委内瑞拉链霉菌 ISP5230 中分离出来的，其特征在于其是一种结构独特的八元 L-鸟氨酸环，含有 Jadomycin。通过使用活化的琥珀酰亚胺酯对 L-鸟氨酸 α-氨基进行化学选择性酰化，对起始材料进行半合成衍生化，从而阐明了该结构。掺入 5-氨基戊酸产生了贾多霉素 AVA，这是另一种含有八元环的贾多霉素。这些天然产物说明了生物合成途径中非酶促步骤所允许的结构多样性，并举例说明了发现新型支架的潜力。
Jadomycin Oct (1) was isolated from Streptomyces venezuelae ISP5230 and characterized as a structurally unique eight-membered l-ornithine ring-containing jadomycin. The structure was elucidated through the semisynthetic derivatization of starting material via chemoselective acylation of the L-ornithine alpha-amino group using activated succinimidyl esters. Incorporation of 5-aminovaleric acid led to jadomycin AVA, a second eight-membered ring-containing jadomycin. These natural products illustrate the structural diversity permissible from a non-enzymatic step within a biosynthetic pathway and exemplifies the potential for discovery of novel scaffolds.