The dynamic structure of Jadomycin B and the amino acid incorporation step of its biosynthesis
The dynamic structure of Jadomycin B and the amino acid incorporation step of its biosynthesis
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DOI：
10.1021/ja031724o
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发表时间：
2004-04-14
影响因子：
15
通讯作者：
Rohr, J
中科院分区：
文献类型：
--
作者：
Rix, U;Zheng, JT;Rohr, J
Jadomycin B是一种由委内瑞拉链霉菌（streptomyces委内瑞拉链霉菌isp5230）产生的具有独特的8H-benz[B]oxazolo[3,2-f] phenantithridine五环骨架的抗真菌抗生素，存在于C-3a构型不同的两种非对映体的动态平衡中。通过取代s .的生产培养基中的异亮氨酸，可以生成几种具有不同氨基酸衍生1侧链的新型jadomycin。委内瑞拉与其他氨基酸。这两个发现得出结论，与氨基酸的非酶反应随后的非酶环化级联对其后期生物合成至关重要。
Jadomycin B, an antifungal antibiotic with a unique 8H-benz[b]oxazolo[3,2-f]phenanthridine pentacyclic skeleton produced by the bacteriumStreptomyces venezuelaeISP 5230, exists in a dynamic equilibrium of two diastereomers differing in the configuration of C-3a. Several novel jadomycins with various amino acid-derived1-side chains could be generated, by replacing isoleucine in the production medium ofS. venezuelaewith other amino acids. These two findings led to the conclusion that a nonenzymatic reaction with the amino acid followed by a likewise nonenzymatic cyclization cascade are crucial for its late biosynthesis.