The Dynamic Structure of Jadomycin B and the Amino Acid Incorporation Step of Its Biosynthesis

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• 作者：Uwe Rix ; Jianting Zheng ; Lily L. Remsing Rix ; Lisa Greenwell ; Keqian Yang ; and Jü ; rgen Rohr
• 刊名：Journal of the American Chemical Society
• 出版年：2004
• 出版时间：April 14, 2004
• 年：2004
• 卷：126
• 期：14
• 页码：4496 - 4497
• 全文大小：110K
• 年卷期：v.126,no.14(April 14, 2004)
• ISSN：1520-5126

文摘

Jadomycin B, an antifungal antibiotic with a unique 8H-benz[b]oxazolo[3,2-f]phenanthridine pentacyclic skeleton produced by the bacterium Streptomyces venezuelae ISP 5230, exists in a dynamic equilibrium of two diastereomers differing in the configuration of C-3a. Several novel jadomycins with various amino acid-derived 1-side chains could be generated, by replacing isoleucine in the production medium of S. venezuelae with 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.