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  • Title: The dynamic structure of jadomycin B and the amino acid incorporation step of its biosynthesis.
    Author: Rix U, Zheng J, Remsing Rix LL, Greenwell L, Yang K, Rohr J.
    Journal: J Am Chem Soc; 2004 Apr 14; 126(14):4496-7. PubMed ID: 15070349.
    Abstract:
    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.
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